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Captiva Island Vacation Rentals: Beach Houses, Villas, Condos, & Luxury Homes

Captiva Island Vacation Rentals: Beach Houses, Villas, Condos, & Luxury Homes

Captiva Island, Florida, is a Gulf Coast gem offering vacationers a serene and picturesque retreat. Surprisingly, for a tiny island, the variety of places to stay on this stretch of beautiful beach is plentiful and offers a wide variety of properties. From budget-friendly to lavish, there is something for all tastes and preferences.


Imagine waking up in an oceanside condo, classic cottage, bayside villa, or private beachfront home and stepping out to the spectacular Gulf of Mexico right at your feet. Browse through our stunning portfolio of Captiva Island vacation rentals, where you will find a multitude of properties, each with its unique charm and equipped with all your creature comforts.

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3

6

$504.00 - $1,100.29

Captiva, FL 33924, USA

INTRODUCING SERENITY A Note To Our Guests: With each new sunrise, we’re one day closer to normal on the islands of Sanibel and Captiva. We’re working diligently with our owners to reopen their vacation rentals as quickly and safely as possible. Please be aware that clean up and construction work will continue throughout the islands due to Hurricane Ian. Hurricane Ian Damages to Serenity: -Privacy fence, on right side only, needs to be replaced and pavers need resurfacing. This will not inhibit your stay. -Landscaping is still getting worked on and workers may be there more than once a week. Live the Island life and experience ultimate island living on Wightman Lane, a private shell lined street located just 4 homes from the pristine beaches of Captiva Island. You are just a short walk to all of the islands favorite restaurants, galleries, shops and local marinas plus live music. Relax as you are surrounded by the lush tropical landscaping with two levels of outdoor living. You will love everything Serenity has to offer! HOME FEATURES This private island pool home features an expansive open gourmet kitchen, dining, and living room area perfect for entertaining or relaxing with family and friends. Flat screen smart TV's are featured in the living area and all bedrooms, as well as free WIFI. Serenity offers a unique 3 bedroom island home which is perfect for a group of 6, including 1 king master suite with ensuite bath along with two private queen bedrooms, one with its own ensuite bathroom. Serenity also features a large caged in heated pool and hot tub for year round enjoyment! Relax on the upper and lower covered terrace areas for outdoor entertaining poolside. Full size laundry room and now offering child booster seat and pack and play. You'll be surrounded in privacy by lush tropical landscaping and gardens, all while being so close to all the action in the village area. Experience this luxury island getaway. Golf cart and bicycle rentals are available nearby to explore Island style! Garage not available for guest use.

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3

10

$640.00 - $893.00

Captiva, FL 33924, USA

INTRODUCING VILLA ELENA NOW HOSTING AND ACCEPTING NEW RESERVATIONS HOME FEATURES Relax and unwind at the beautiful Mediterranean-inspired Villa Elena. Located on the iconic Tween Waters stretch of Captiva Island, this house has access to both the pristine Gulf beach and the abundance of wildlife on the bay. There is plenty of room for a large family or group, comfortably accommodating up to 10 people. Everyone will enjoy the recently updated décor and the open single-story floor plan containing four bedrooms and three bathrooms. The light-filled master bedroom has a king-sized bed with an en-suite bathroom and French doors leading to the tropical courtyard. The second bedroom has a queen-sized bed with en-suite bathroom. Third bedroom has two twin beds along with en-suite bathrooms. There is a fourth bedroom containing two twin beds. The living room offers a new queen sleeper sofa and smart TV. The updated kitchen with granite counters offers plenty of room to gather. You will find it is well equipped for all your cooking and entertaining needs. When your meal is ready, enjoy it in the oversized dining room or in the screened-in terrace complete with a dining table, lounge area, fountain and fireplace. No usage of fireplace please, fountain switch to turn on and off is located in master bedroom. A short walk down your shell lane leads to either the beach or the bay for island fun. Enjoy some relaxation at the house in your private heated pool. Poolside loungers and market umbrellas are provided for your outdoor comfort. Villa Elena has a washer and dryer, gas BBQ grill, cable/WIFI, beach cart with beach chairs and umbrella, plenty of pool and beach toys, board games and books. Located very close to the shops and restaurants in Captiva Village Square, and only a short 5-minute walk to ‘Tween Waters Island Resort and Spa. Sanibel Captiva Island Vacation Rentals is here to make your vacation everything you hope for! HAVE QUESTIONS? Call the Sanibel Captiva Island Vacation Rentals Team for more information, including a list of local vendors that rent items such as bicycles and baby equipment.

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1.5

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$384.00 - $600.00

Captiva, FL 33924, USA

INTRODUCING THE SHORE BIRD Brand new to a rental program! HOME FEATURES: Experience the ultimate island getaway with The Shore Bird guest home! This beautiful home is located along the island's Captiva Drive offering breathtaking views of the bay and pristine beach on the Gulf of Mexico. The Shore Bird features a spacious living area, Queen sized primary bedroom with ensuite bathroom, and modern decor. Adorned with a fun filled family room the sofa also serves as a pull-out sleeper. This home is the perfect place to relax and unwind, whether you're looking for a romantic getaway or a fun-filled family vacation. Enjoy your own private heated pool, boat dock, and deeded beach access just steps away from your front door. The Shore Bird guest home has everything you need to make your stay unforgettable. Book now and experience the ultimate island escape!

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9

$389.86 - $1,079.29

Captiva, FL 33924, USA

INTRODUCING THE ROYAL PALM HOUSE HOME FEATURES This three-bedroom home is situated on the Silver Palms Estate and is tucked away on the Roosevelt Channel, giving you a peaceful and relaxing feel and is every fisherman's dream with a private dock, private heated pool and full resort access to Tween Waters Island Resort and Spa, only 0.5 miles away! This home can sleep up to nine guests and is dog friendly with owner approval (additional pet fee applied). As you drive down the driveway and through the tropical foliage, you will be welcomed by the private pool to Royal Palm and the house's elegant and tall structure. As you enter up the stairs and through the great room, you'll immediately notice the exquisite views of the Roosevelt Channel and open floor plan. Enjoy the chef's kitchen, large living room and the large private balcony overlooking the dock and water. The living room features a sleeper sofa for two and a chair sofa for one (good for kids). The Royal Palm house features two guest bedrooms on the main floor, both equipped with a king bed and ensuite bathroom. One of the guest bedrooms also has its own private entrance to the balcony, overlooking the dock. As you walk up the stairs to the master suite, you'll notice a large workspace that is perfect for setting up a laptop and is great for someone who needs to get some work done during their stay. The master suite is equipped with a king bed and has its own private balcony that is partially covered and partially open for sunbathing. Indulge yourself in the breathtaking master bathroom with a non-jetted soaking tub, spacious walk-in shower and huge walk-in closet. It's a master suite you could only dream of! The heated pool is located in the front of the house and has plenty of space for swimming, sunbathing and playing games. **ONE OF THE BEST FEATURES OF THIS HOME IS HAVING FULL RESORT ACCESS TO 'TWEEN WATERS ISLAND RESORT AND SPA** Have a larger group? No worries! Coconut Palm House is on the estate and is also available to rent! Both homes can sleep up to 21 people, have 2 private pools and room for 2 boats at the private dock! You can't get any better than this!

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$777.57 - $1,818.00

Captiva, FL 33924, USA

INTRODUCING ROOSEVELT COTTAGE: NOW ACCEPTING RESERVATIONS HOME FEATURES Roosevelt Cottage is located on Captiva Island .1 miles from ‘Tween Waters Island Resort & Spa. This home features an open floor plan for extended family and friends with a spacious living area opening into the chef's gourmet kitchen with 4 burner gas range, upscale appliances and breakfast area. The northern wing in the main house features a primary king bedroom suite, TV and en-suite bathroom with claw foot tub, shower and walk in closet. This wing also offers a spacious office area with TV and half bath which is convenient to the master suite. The main level also features a formal dining room an additional den with TV off of the kitchen area plus a large laundry room providing two sets of stack washer/dryers for your convenience. The property features an expansive screened lanai overlooking the dock and Roosevelt Channel. The upper level of the main home offers a spacious loft with comfortable queen size sleep sofa and a flat panel TV. There is a guest bedroom on each side of the loft both with queen sized beds and a full bathroom with a tub/shower combination. Just outside the main home is the charming guest cottage which was the original fishing cottage on this tropical oasis. The guest cottage offers a quaint living area with TV and WIFI and a handy kitchen with a refrigerator, stove and microwave plus a dining area. The guest cottage also has a comfortable sleeping area with a king-size bed, full bathroom and utility room with a washer and dryer. For additional family and friends, there is a carriage house guest suite which sleeps 2 with a king size bed, full bathroom and spacious seating area equipped with flat screen TV. A morning kitchen in this suite is convenient for guests. This suite is located above the carriage garage. Roosevelt Cottage has plenty of space with nearly 5,000 sq ft of space combined in three separate structures. Our favorite feature and center of attention you will find the private heated pool hidden among the lush mature vegetation with a waterfall. Roosevelt Cottage offers a large private boat dock and fishing pier. This estate home is a hidden gem you and your family will treasure while enjoying the perfect vacation destination. Roosevelt Cottage estate offers extended family and friends many options for sleeping and providing a relaxing atmosphere and privacy.

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$500.00 - $700.00

Captiva, FL 33924, USA

INTRODUCING CELEBRATION HOUSE VILLA A NOTE TO OUR GUESTS: With each new sunrise, we’re one day closer to normal on the islands of Sanibel and Captiva. We’re working diligently with our owners to reopen their vacation rentals as quickly and safely as possible. Please be aware that clean up and construction work will continue throughout the islands due to Hurricane Ian, and so work that has been scheduled for this home cannot be cancelled or rescheduled. Service providers for internet, cable and pool concerns may not be available during your stay. There are limited housekeeping and maintenance services. Rest assured, this home is cleaned and ready for your arrival. There is no guaranteed internet or cable which makes this season the perfect time to unplug, unwind and explore the local business community. There are ribbon cuttings each week across the islands to celebrate grand reopening's — and they’re all incredibly excited to meet you. And remember, stay stress-free when it comes to relaxing on the beach as you’ll have access to ‘Tween Waters Island Resort & Spa’s private, pristine Gulf of Mexico beach on Captiva Island. HOUSE FEATURES This 3-Bedroom Villa encompasses the entire 2nd floor of The Celebrations House, a 5,000 square foot home located in the heart of Captiva Island, Andy Rosse Lane. This villa is not shared space amongst other guests. Consider it your private villa with all the benefits of home - and more. Featuring a fully equipped kitchen with granite countertops, stainless appliances, and gorgeous wood cabinets, a large living room, dining area, 3-bedroom suites, and 2 porches, this spacious villa has it all. Each of the 3 bedrooms has a king-sized bed, TV, an ensuite bathroom and a private outside entrance with a door that opens into the den area, for maximum privacy and comfort. Perfect for a family vacation or 3 couples, this 3-bedroom Villa at the Celebration center is located just a hop, skip, and jump away from one of America's most magnificent shelling beaches, Captiva Island Beach; so be sure to bring your sunscreen and shelling supplies! The Celebration center has the perfect location, sitting between the Captiva Island beach and the bay guaranteeing that either way you go, there will be plenty to see and do with award-winning restaurants within walking distance, quaint shopping and more. HAVE QUESTIONS? Call the Sanibel Captiva Island Vacation Rentals Team for more information, including a list of local vendors that rent items such as bicycles, golf carts, and baby equipment.

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4.5

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$692.00 - $1,439.00

Captiva, FL 33924, USA

INTRODUCING COCONUT PALM HOUSE On the Captiva Drive stretch, Coconut Palm is an elegant and luxuriously styled home that can sleep up to 12 guests (eight adults comfortably) and is dog friendly (with owner approval). Coconut Palm offers five bedrooms and four and half bathrooms, your own private pool, dock and full access to 'Tween Waters Island Resort and Spa, only 0.8 miles away, this home has everything you need for a week or longer vacation! Have a larger group or family? No worries. The Royal Palm House is on the same Silver Palms Estate and is also available to rent! Both homes can sleep up to 21 people, have 2 private pools, and room for 2 boats at the private dock! You can't get any better than this!  HOME FEATURES As you drive down the driveway and through the tropical foliage, you'll immediately feel like you're at your own island oasis. As you walk through the front doors and up the stairs, you'll be welcomed to the open living room and kitchen area that has room for the entire family to cook and relax. Off from the living room is the entrance to your private balcony, overlooking the screened-in pool. A perfect place to enjoy your morning coffee or afternoon lunch while the kids enjoy the pool.  Coconut Palm features a king in the master bedroom, located on the main floor and off from the living room, with an ensuite bathroom and a large walk-in closet. The 2nd guest bedroom features a double bed and is also off from the living room and can be closed off from the master suite. As you walk up towards the 2nd floor, you'll notice a small den area that features a trundle bed, perfect for the kids! The 3rd bedroom is equipped with a queen bed and ensuite bathroom and 4th bedroom has 2 twins and ensuite bathroom as well.  Downstairs is perfect for additional sleeping space and is where a lot of the fun can take place. In the main area there is a pool table and sitting area with bar nook and mini-fridge. There is also a door that leads out to the enclosed pool. The other side of downstairs can be completely closed off and features a full bath, full kitchen, washer and dryer, sitting area and a trundle bed. There is also a guest suite that features a queen bed. This area is considered the 5th bedroom.  **ONE OF THE BEST FEATURES OF THIS HOME IS HAVING FULL RESORT ACCESS TO 'TWEEN WATERS ISLAND RESORT AND SPA**

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10

$828.60 - $1,121.45

Captiva, FL 33924, USA

INTRODUCING HARBOUR HOUSE Welcome to Harbour House Captiva. This coast casual living home has undergone extensive renovations so that guests can experience an upscale and wonderful stay while on Captiva Island. Located in the historic Captiva Island village area you are just a short walk to all of the island's best restaurants such as the Keylime Bistro, R.C. Otters and Cantina Captiva, Mucky Duck and the Bubble Room. Enjoy the island music along with shopping and marinas. Golf cart and bike rentals are nearby to explore on your island adventure. Harbour House of Captiva continues to be one of Captiva Islands' best vacation rental homes available. HOME FEATURES This island oasis offers relaxed island living with a spacious floorplan, heated pool, hot tub and private dock. The main level of the home has an updated living room, family room, dining area, full kitchen and laundry room. There is an expansive screened lanai overlooking the pool and beautiful bay waters for relaxed outdoor living. Enjoy the open porch for grilling your fresh catch of the day. Up the staircase is an open loft with two twin beds along with 3 king bedrooms and 1 queen bedroom with plenty of space for up to 10 guests. Great family vacation getaway. Master suite is handicapped equipped with roll in shower. The dock does have electric and water. Lift not available for guests. HAVE QUESTIONS? Call the Sanibel Captiva Island Vacation Rentals Team for more information, including a list of local vendors that rent items such as bicycles, kayaks, and baby equipment.

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$649.80 - $1,280.11

Captiva, FL 33924, USA

Bird of Paradise sustained little damage from hurricane Ian. The home had been repaired and is ready to Welcome Guests starting Feb 4th 2023. Book your stay today and get the first right to rebook your week for 2024.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!Bird of Paradise is located in the heart of Captiva Island yet offers privacy and comfort. Central to the beach, shops, restaurants, marinas, live music, bars and watersports. This tranquil four bedroom home sleeps ten comfortably. Walk into the main living with soaring white washed ceilings that give the home a comfortable beach feel. Relax in the spacious living room with plenty of seating for family and friends, a flat screen television and open concept into the dining-room. Enjoy the gorgeous dining room table with seating for eight. The large updated kitchen is off of the dining room has beautifully painted cabinets and is perfect for creating amazing meals or heating up take out from the delicious Captiva restaurants. On this level there are two guest bedrooms and two bathrooms. The first bedroom has a comfortable queen bedroom and the second bedroom has two comfy twin beds. The master suite on this third floor features a comfortable king bed, a private deck and a large master bathroom with granite countertops and a walk in shower. The fourth bedroom is on the lower level with a king bed, television and a day bed, this area is very private with its own entrance. The large heated pool is the perfect area with tropical landscaping, a pool cage. It is the perfect spot to relax and enjoy the amazing weather. The game area underneath the house features a ping pong table and pool table. Just two homes down from the beach path which takes you past the charming Chapel by the Sea to stunning white beaches. Bird of Paradise has everything you need for an amazing family beach vacation. Book this home today, you will be thrilled with your choice !Property Manager will only book reservations up to 51 weeks in advance.

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10

$2,170.56 - $4,105.14

Captiva, FL 33924, USA

Life Changing Views in this four-bedroom LUXURY bayfront home. Currently getting new flooring throughout and new bedroom furnishings. Truly one of a kind long range view of Pine Island Sound where dolphins and manatee play. Relax by the heated pool with the water views. World class fishing from the huge dock. Multiple decks, outdoor kitchen as well as the interior gourmet kitchen. Easy tie up for a large boat. Enjoy sunset strolls along the world renown beaches of Captiva. The ultimate home for memory making vacation.More photos and description to follow as the new furniture and flooring is completed. Book your weeks today!

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$1,429.56 - $2,079.36

Captiva, FL 33924, USA

Hakuna Matata- No Worries as you experience this beautiful 5-bedroom/6-bathroom Captiva channel front home. The perfect location to bring your boat, walk on the beach, relax in the pool, or lounge on the many decks with water views.Included in the rental is a free sightseeing or lunch trip by boat for up to six people from 10 a.m. to 2 pm with one of the best guides in SW Florida! Get on the schedule early.Kayaks are also included for free with your stay!As you walk up a small set of stairs to the main living area you will notice the amazing views of Roosevelt Channel, the large living room with high ceilings, and the open dining and kitchen. Plenty of room to be comfortable with a large family and two dining tables to enjoy memorable meals together.This spacious home features three master suites with king beds. The first King suite is in the main living area with an area to the expansive back deck.This master bathroom features a bathtub and shower combo. Also on this level is a queen bedroom with its own bathroom. Another king bedroom with its own bathroom.The top floor features another large master suite with stunning views, a walk-in closet, and a master bathroom with a separate bathtub and shower. This floor also features another guest bedroom with two twin beds and an attached bathroom. On the lower level, there is a bunk room with full and twin beds. The lower-level garage is full of fun toys for the whole family to enjoy! Bikes, sand toys, pool toys, and more. Kayaks are included at no extra charge.Beach access is a short stroll down the newly landscaped path and across the street. Enjoy stunning sunsets from the white sandy beaches of Captiva Island.Free KayaksFree BikesFree Golf CartFree Beach CartFree Beach Fishing Cart**Landscaping has changed since Hurricane Ian. New plants have been installed but will need time to grow**

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$649.80 - $1,169.64

Captiva, FL 33924, USA

Built in 1953, this 3,000-square-foot mid-century modern house with great amenities, while preserving the relaxing appeal of a 1950's beach home. Its open floor plan is great for relaxing with the family, playing games, and creating lasting memories. The enclosed porch with old Captiva charm perfect for sunset viewing is complete with a round table, chairs, and beautiful wood finishes. This is the perfect spot to watch the most stunning sunset you have ever seen.Take a small step up into the open floorplan living room, dining room, and kitchen. The brick fireplace features unique artwork and a large flat screen television. The sectional couch and extra chairs are a great spot to curl up and watch your favorite movies after a long day at the beach. The open kitchen is the perfect spot to create a great meal while still enjoying friends and family in the living room. The floors in the main area of the home are original tile from the 1950’s.Large cabinets, a coffee bar, tall counters, and updated appliances will supply you with everything you will need to cook a fresh meal or store and reheat leftovers. The kitchen also opens to the dining area with a large table and seating for eight.The first queen bedroom is located off the dining room and features views of the beach. This bedroom has its own private bathroom that was recently remodeled with coastal tile accents. A flat screen television and couches make this a great bedroom for family and friends.Take the short stairs down to the spacious second bedroom which is great for children or an entire family that is brightly decorated with two twin beds, a queen bed, a flat screen television, and a large window seat. Take the short stairs up to the second floor featuring two bedrooms each with their own bathrooms. The first bedroom features two double beds, the private bathroom, and flat screen television.The second bedroom has a king bed, the private bathroom, and a private lanai overlooking the pool. The enclosed lanai is at the perfect angle for a morning coffee while you watch the colors of the sunrise and their reflection on the pool.The pool is large, 32-by-16-feet, heated, and naturally landscaped. It has a roomy shallow wading ledge perfect for kids to play and splash around in. After steps, the pool gently slopes to a depth of six feet, with additional ledges on the sides for sitting and relaxing. There are two outdoor showers, great for washing the sand off before entering the home. Amenities include a washer and dryer, 4 flat screen TVs, 1 large flat screen smart TV, 2 DVD players, a stereo, wireless speakers, and high-speed wireless internet throughout the home.Baybarlyn is an older beach home that is the perfect place for both large and small gatherings. Stroll along the dock path while enjoying the tropical plantings unique to the islands. The dock is a great spot for some of the best fishing in the area. Right across the street is the home's private beach, a lovely place to relax, read, or play in the surf. Captiva features world-class shelling, so you will easily find a few treasures to take home with you. As the day melts into the night, enjoy our stunning sunsets and stargazing is second to none on Captiva Island. The properties distance from the mainland keeps the light and noise pollution to a minimum, allowing the stars to dominate the night sky and the sea breeze to be the only sound heard for miles.If you desire a night in, there are large screen TV's, Xbox, a game closet, and access to high speed Wi-Fi throughout the house. If you're looking for fun island excursions there are many options within easy walking or biking distance. Nearby 'Tween Waters Inn hosts crab racing on Mondays and Thursdays. Local art galleries such as Jungle Drums display the works of island and mainland artists and craftsmen. The island has several marinas where you can rent a boat to cruise around the islands and up the Inter-Coastal Waterway. Bring your own boat and moor it at our shared dock in the back bay, a haven for sport fishing. If you enjoy kayaking, you can rent one from various locations on both Captiva and Sanibel. Spend the day exploring the numerous bays and mangrove trails, such as the newly reopened Buck Key. Restaurants such as The Mucky Duck, The Green Flash, and Key Lime Bistro ensure that visitors with a desire for delicious food will not be disappointed. For dessert, pick up a giant slice of cake or pie from The Bubble Room, a quirky, 1930s-themed restaurant near the heart of the town. During the winter, visitors are welcome to attend services at the Chapel by the Sea. Services are held in a charming one-room schoolhouse-turned-chapel. Sanibel Island is home to Ding Darling Wildlife Refuge and Clinic for the Rehabilitation of Wildlife (C.R.O.W.). These places are wonderful for learning more about the islands and local wildlife. Ding Darling has a beautiful wildlife drive, several walking paths, and is well known for its fantastic birdwatching. Tarpon Bay Marina and Wildlife, affiliated with Ding Darling, has a sea animal touch tank and gives educational boat tours of the protected bay area lead by Marine Biologists. C.R.O.W. also features many educational programs. Whether you seek a warm, relaxing getaway during the winter or a fun-filled family vacation in the summer, Baybarlyn with its enchanting tropical charm will delight you.Property Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!

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9

$519.84 - $681.72

Captiva, FL 33924, USA

This three bedroom townhome is updated and spacious, perfect for a large or multiple families. Located on the stretch of Captiva where you can walk from the bay to the beach in about four minutes. A peaceful location that is walking distance to shops, restaurants, marinas, live music, shopping and watersports. This three bedroom townhome features an updated kitchen with granite countertops and breakfast bar. The open dining room and living room has cathedral ceilings, soft and cheerful décor, wood floors and seating for nine. The spacious living room features a flat screen television, two comfortable couches and sliding glass doors to the lanai with water views. The large lanai has a table with seating for four, views of the dock and the bay, views of the pool and a stairway leading to the tropical grounds. The first guestroom on the main level has a queen bedroom flat screen television. The main floor bathroom is shared by this guest bedroom. The second bedroom on the main level is the master suite with king bed, amazing views and an en suite bathroom with dual sinks and tiled shower. The third bedroom is located on the second floor with two twin beds and a shared bathroom with shower/tub combination. The upstairs also features an open office with more views.The grounds of Ventura Captiva are well maintained with a large heated pool, fishing and boating dock. Located just minutes from the beach this is the perfect location to experience everything Captiva Island has to offer.Property Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!***Literally steps to the beach, this 10 unit Bayfront complex has a lot to offer. Enjoy relaxing by the pool or spend your days exploring Captiva by land or by sea. The community shares boat docks which make it easy to enjoy a day on the water.

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$935.94 - $1,566.36

Captiva, FL 33924, USA

** Caretaker on site in separate house**Little Current sustained little damage from Hurricane Ian and will be ready to Welcome Guests starting February 4th,2023. The landscaping was damaged during the storm and has been replanted but with take a few months to regrow. Book your stay today and get the first right to rebook your week for 2024.The ideal home to experience the best of Captiva. This three-bedroom three-bathroom pool home with a hot-tub is updated and spacious. Little Current is located right on the water of Blind Pass. This means the best fishing on the island, amazing views, stunning wildlife, and special memories to be made. Multiple decks with beautiful views, an expansive dock for fishing, tying up a boat or launching a kayak. Walk into the home to a large sitting room with vaulted ceilings and coastal décor. The updated kitchen features solid surface countertops, new appliances, and everything you need to create an amazing meal. The kitchen is open to the comfortable family room with plenty of seating and a flat screen TV. The open dining area has seating for four at the table with additional seating for three.The first guest room has two twin beds and a bright clean décor. The second guest bedroom features a queen bed. The guest bathroom has a shower/tub combination. The large master suite features a king bed, flat screen TV and attached bathroom with shower.Beach access is right across the street. Blind Pass beach has STUNNING sunsets and is world renowned for its beauty.Spend your days relaxing by the saltwater pool, fishing off the dock, strolling along the beach or walking to the local restaurants. This is truly a special home that you will not want to miss.Property Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!2 Kayaks are available for rental for an additional fee of $350 per week please email or call to add this to your reservation. The dock can accommodate a 25-foot boat to be tied up along the inner portion of the dock.

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$487.35 - $714.78

Captiva, FL 33924, USA

**Lollipop is considered a value property which means great location, good interior but some worn fixtures and some worn exterior**Lollipop, the perfect Captiva vacation home. Central to Captiva village this three bedroom three and ½ bath pool home offers the perfect escape for a relaxing vacation. There are so many great features to this home, cathedral ceilings, screened in porch, updated modern kitchen, pool and spa and multiple decks. A short three minute stroll down sandy Laika Lane and you will be on the world renowned beaches of Captiva. The master suite features a comfortable king size bed and large shower in the master bathroom. The first large guest room features ample space a comfortable queen bed and bathroom in the hallway. The second guest room has a double bed and ample closet space. A day bed off of the living-room with a trundle is a comfortable space for your guests. The third full bathroom is located off of the dining area on this main floor. Relax by the pool, walk to the beach, walk to restaurants and marinas. The perfect location for the perfect vacation.Property Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!

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$636.12 - $941.64

Captiva, FL 33924, USA

2 Minute Walk to the BeachEscape your worries in this Captiva Island beach bungalow. Enjoy the bright and cheery island décor throughout this three-bedroom two bath pool home. Surrounded by bright tropical vegetation, this home offers a perfect location to the Heart of Captiva as well as ultimate privacy. Equipped with everything you need to enjoy your vacation this bungalow features vaulted ceilings, tile floors in the living areas, a 47 inch flat screen TV in the great room, two DVD players, televisions for each bedroom, Wi-Fi, a fully equipped kitchen with a large refrigerator, dishwasher, range, washer, dryer and dining table for six. The relaxing master bedroom has a king-sized bed, master bathroom with shower and its own private patio. The first guest room has two closets and two comfy twin beds. The 2nd guest room has a queen bed and sliding doors that look out over the tropical pool. Spend your days relaxing by the large screened in pool, reading a book in the screened in patio or walking on the beautiful beaches. Spend your nights enjoying the delicious island restaurants, watching amazing sunsets or listening to a local musician play tropical tunes. A truly perfect location “Wait N' Sea” is just minutes to the beach, the bay, the local marinas, and restaurants yet offers the seclusion of a private home.Reme Halo air disinfection system installed in the central ACProperty Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!

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$857.28 - $1,403.34

Captiva, FL 33924, USA

Completely repaired and ready to Welcome Guests !Amazing Location! This five-bedroom, five-bathroom pool home is central to Captiva Village, marinas, restaurants, shops and live music. This home had recently been updated new furnishings and décor, new stairs, new carpet, and the wood floors have been redone. The pool is new with new tile, new landscaping, new exterior décor and the house has been freshly painted.A large kitchen with an open living, dining room, high ceilings, and a screened in pool. The five bedrooms have ample room for all guests to relax after a day at the pool or beach. Just a 5 min walk (.1 mile) to gorgeous Captiva Beaches!Elevator not available for guests.Property Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)!

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$1,559.52 - $3,638.88

Captiva, FL 33924, USA

The Total Experience! Yes below is all included in this rental!Sunset Captiva Cruise for 14!An evening with a private Chef!Online grocery delivery at your fabulous home when you arrive!Free taxi ride from RSW (Fort Myers) airport!Free six-person golf cart!Free beach equipment!IL Paradiso Perduto is a seven-bedroom luxury home located in the center of Captiva Village. Just a minute's walk to the beach! This home has no damage from Hurricane Ian and is ready to Welcome Guests! New to the rental market so book your weeks today and get the first right to rebook for 2024.As you walk into the main level of this stunning luxury home you will notice the incredible ceilings, beautiful woodwork, tile floors, and rich decor. On your right, you walk into the first hallway that features a guest bathroom with beautiful, tiled floors and an antique vanity. On this wing is a large Butler’s pantry with an additional dishwasher, refrigerator, and top-of-the-line washer and dryer. Walk along the hallway with its bay window offering upholstered seating to gaze over its stunning courtyard. Continue to the queen bedroom with its own private bathroom whirlpool bathtub, separate shower, double sink vanities, and beautiful tile work. There’s also a walk-in closet and a small balcony overlooking Andy Rosse Lane. The bedroom also features a flatscreen television, high ceilings, beautiful decor, and a ceiling fan. On this level, you will also find a beautiful office with a computer monitor and keyboard ready for all of your work-at-home needs. There’s a large wood desk and additional storage with beautiful tray ceilings, faux wood tile floors, and huge windows. This main area also has a large open living room with flatscreen television. A beautiful bar with a wine cooler dining for 8 to 10 and a large open kitchen. This stunning kitchen features one-of-a-kind tile wood floors, top-of-the-line appliances, double ovens, a warming drawer, a gas stove, a sub-zero fridge, and a Bosch dishwasher. There is also a Keurig and regular coffee maker. Create a fabulous meal or heat your leftovers while dining in the small breakfast nook with the windows overlooking tropical grounds. The living room opens up to the center courtyard overlooking the pool, expansive decks, outdoor fireplace with television, outdoor kitchen with gas grill, and outdoor bar including outdoor seating. This special area provides a pool, hot tub, tile floors, outdoor kitchen, outdoor seating, and outdoor dining all within the privacy of the courtyard. A separate suite is off of this main level courtyard with a balcony, flatscreen television, queen bed, and an attached bathroom with a shower. Up the tumbled stone stairs to another stunning hallway with beautiful decor a master bedroom featuring a king bed, flat screen television, built-in bookshelves, a huge built-in custom dresser, walk-in closet, en suite bathroom with a jetted tub, his and her sinks, tiled shower, and custom cabinets. This master suite also opens up to the upper deck overlooking the center courtyard and pool area.The second bedroom on this level features a queen bed, large closets, double doors opening up to the upper balcony, and an en suite bathroom featuring a walk-in shower with views of the courtyard and pool. The first-floor bottom level is centered around a stunning pool with a hot tub and a relaxing waterfall with multiple decks. This level also features a large television room with a huge flatscreen TV, pool table, popcorn machine, and stunning views of the pool, there is a large bedroom with two full beds, flat screen television, huge closets, and an en suite bathroom with a tiled shower.This lower level also features another guest bedroom large walk-in closet, two twin beds, and an en suite bathroom with a large soaking tub shower combo. This level also features another guest bedroom with a queen bed, large flat screen television, an en suite bathroom with a large soaking tub and shower also large closet space.

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$2,508.23 - $4,873.50

Captiva, FL 33924, USA

Reduced Prices for Winter of 2024! On top of the reduced prices now included in the rental for free:** Six Seat Golf Cart for additional $500 per week- Now Free!** Golf carts are allowed in Captiva Village to Tween Waters but no further than Tween. **Two fishing kayaks available to rent for an additional $425.00 per week- Now Free! ** ** Two Stand Up Paddle Boards available to rent for $300 per week- Now Free! **Captiva Grace is ready to Welcome Guests! While the home sustained very little damage from hurricane Ian the large hedge in front of the home had to be removed. The pool is sparkling clean, the home is still stunning, and the beach is open and beautiful. Book your stay today and get the first right to rebook your week for 2024.GULF TO BAY! One of the few properties on Captiva Island that span from the Gulf of Mexico in front to the Bay in the back. Boasting stunning luxury, this 5-bedroom 5.5 bathroom home truly has everything. Wake up to a beautiful sunrise from the dock overlooking the bay with your morning coffee. Wind down to a stunning sunset while enjoying a cocktail on your semi-private beach located steps from the home, directly across the lazy island road.You may also choose to relax on one of the multiple decks or alongside the heated pool with a view. The large, private dock is perfect for a 20+ foot boat, launching a kayak and some of the best fishing on the island. Don’t have a boat? Local fishing guides will pick you up right from your dock!Walking into the main floor, you are greeted with a large open floor design showing off views of the gulf, with a living area, dining for 10, wet bar, kitchen, and beautiful décor. The modern kitchen has everything you need to make a fabulous meal and overlooks the Bay, pool, and private boat dock. The comfy family room has a flat screen TV and enjoys more floor to ceiling views of the Bay. This level also includes a den with Gulf views, bathroom, and a sleeper sofa.The second floor boasts two beautiful master suites plus two additional guest bedrooms. The first master suite showcases stunning floor to ceiling views of the Bay, a king bed and flat screen television. The large, tiled master bathroom has dual sinks and a separate tub and shower. The second master bedroom faces the Gulf with a king bed and private bathroom. The first guest bedroom suite includes two twin beds, a flat screen television and views of the Bay and the second guest bedroom suite contains a king bed, attached bathroom and additional Bay views.The first-floor level has a spacious guest bedroom with two queen beds, flat screen Tv and double doors to the heated pool. A full bathroom is also located on this level with entry off the garage.Also included: Sono’s system throughout, garage, ice maker, elevator, gas grill, laundry room, beach chairs and beach towels.A beautiful home with true luxury and everything you desire for a once in a lifetime island vacation.Property Manager will only book reservations up to 51 weeks in advance.All our properties have contact free check-in, no need to stop at the office (or a stop light none of those here)! *Boat lift is not available to guest*

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$1,039.68 - $1,773.84

Captiva, FL 33924, USA

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Explore Vacation Rentals in Captiva, Florida

Captiva Island, nestled in the Gulf of Mexico just off the coast of Florida, is a hidden gem known for its natural beauty, pristine beaches, and tranquil environment. Our Captiva Island vacation rentals offer an enticing array of choices for experiencing this enchanting island. From small beachfront cottages to luxurious villas, you’ll find Captiva Island rentals all the coastal charms, including direct access to the island's sugary white sands and crystal-clear waters. Whether you're envisioning a romantic getaway or a family retreat, we’re proud to offer you a range of outstanding options. Spacious rental homes, some with private pools, provide an ideal setting for larger groups or extended stays. Many vacation rentals on Captiva Island are equipped with modern amenities so that you feel right at home. No matter what you choose, our professionally managed portfolio or properties ensure a memorable and stress-free oceanside escape.



Your Guide to Captiva

    What to do in Captiva, Florida

  • Known for its pristine beaches, charming wildlife, and laid-back ambiance, Captiva offers a range of experiences. With so many open-air activities to enjoy, it’s a haven for outdoor enthusiasts. Get your gear ready and begin your day out on the water fishing, or explore your wilder side with some water sports like parasail rides, jet skiing, and paddleboarding along the tranquil bays. After a day of adventure, indulge in the island’s renowned dining scene before relaxing in the comfort of your Captiva rental, where you can savor the island's captivating sunsets. Here are some of our favorite things to do on Captiva Island:


    Start your day beachcombing and shelling: Stroll along the shoreline to find unique treasures washed up by the Gulf of Mexico. The beaches are a paradise for shellers, a long-standing tradition on the island.


    Go on a guided wildlife tour: Revel in the wonder of wildlife encounters with a guided tour of the Darling National Wildlife Refuge on nearby Sanibel Island. It’s a great way to spot dolphins and manatees and the ideal way to enjoy some birdwatching, too.


    Visit The Bailey-Matthews National Shell Museum: Located a short drive away on Sanibel Island, you’ll see more than 30 wonderful exhibits showcasing some of the world’s largest and rarest shell specimens.

  • Best time to visit Captiva, Florida

  • Captiva Island, Florida welcomes visitors all year round, thanks to its tropical climate. Winter tends to be the busiest season, as people go in search of winter sun and some much-needed R&R. However, if you're looking for the warmest weather, sunniest days, and the best beach conditions, the best time to visit Captiva Island is during the springtime, March through May. Summer, from June to August, is a popular time for family vacations, featuring festivals and watersports. Meanwhile, Fall, from September to October, is quieter, with pleasant temperatures, making it great for those who prefer a more peaceful retreat. No matter when you visit, Captiva Island's quiet atmosphere, abundant waterways, stunning beaches, and wildlife are available to enjoy every season, meaning you can enjoy the island’s charm, whatever the weather.

  • The Weather in Captiva, Florida

  • Captiva, Florida, boasts a year-round tropical climate, making it an inviting destination for sun-seekers at all times of the year. Summers, from June to September, are the driest months; it's hot and humid, with temperatures occasionally exceeding 90 °F (32 °C). Lightweight, breathable clothing, sunscreen, and swimwear are essential during this time. Fall, from October to November, sees slightly milder temperatures, and it's advisable to bring light layers for cooler evenings. Winters, from December to February, are the most comfortable, with temperatures in the mid-60s to low 70s °F (15 to 21 °C). While a light jacket may be needed for occasional cooler nights, it’s a great time to enjoy leisurely strolls on the beach and outdoor activities. Spring, from March to May, is pleasant and warm, with balmy temperatures in the high 70s to low 80s°F (21-26 °C). Casual, beach-friendly attire is the norm on this beautiful island, regardless of the season, so don't forget your sunscreen, sunglasses, and a comfy pair of shoes for exploring the island.

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Captiva, Florida Vacation Rental FAQs

  • What are the Different Types of Vacation Rentals in Captiva Island, FL?

    The most popular options for Captiva Island rentals are those which are located on the beachfront. These properties offer direct access to the stunning Gulf of Mexico and unobstructed views of the ocean. You can find spacious beachfront houses that can accommodate large families or groups, providing all the amenities for a luxurious island experience. Waterfront villas are also highly sought after as you can expect to enjoy your own private dock and spacious, private outdoor spaces, making them the ideal haven for those wanting to immerse themselves in island living.


    Other than a small downtown, Captiva has avoided mass development and remains largely a combination of coastal mangroves, trees, forests, and ocean bays. However, many modest homes and historic cottages are available on quiet streets only blocks from the main village. Even modest house rentals on Captiva Island still offer comfort and proximity to the beach, making them an excellent choice for couples or smaller groups.



    Additionally, you can find a variety of other property types, such as apartments or condos, which offer their own unique appeal and amenities. Some even boast highlights like ocean views and private access to balconies that overlook the sea.


    Captiva Island vacation rentals are diverse and plentiful, catering to a wide range of budgets and preferences, so you can rest assured that you'll find the perfect property to make your island retreat a memorable one.

  • What type of amenities should I expect when booking Vacation Rentals in Captiva Island?

    The most popular amenities in Vacation rentals in Captiva are private, heated swimming pools, air conditioning, direct Gulf views, hot tubs, a grill area, WiFi, and an equipped kitchen.

  • What is the best area to stay when traveling to Captiva Island, Florida?

    The most popular choice is the Captiva Village area, which offers easy access to beaches, dining, and shopping. Other options include secluded beachfront properties, bayfront rentals, and marina access, allowing travelers to select the setting that suits them best.

  • How can I get to and around in Captiva Island, Florida?

    There are three airports near Captiva Island. These include The Southwest Florida International Airport, Punta Gorda Airport, and Naples Airport. You can then rent a car or take a taxi or rideshare service to get to Captiva Island via the mainland and Sanibel Island. One of the most wonderful things about the island is that there aren't many cars so the best way to get around and live like a local is by foot, bicycle, or golf cart.

  • Are there pet-friendly house rentals on Captiva Island?

    Yes, there are pet-friendly houses for rent in Captiva Island. However, specific pet policies, restrictions, and fees may vary by property, so it's advisable to check with your Captiva rental manager for detailed information about accommodating your furry friends.

  • Are there vacation rentals on Captiva Island suitable for groups?

    Yes, there are options suitable for groups in Captiva, Florida. Vacation rentals on Captiva Island often include spacious homes, villas, or condos perfect for accommodating larger groups. However, the exact capacity and amenities may vary, so it's recommended to check with the specific property for details.

  • How much do Captiva Island rentals cost?

    The price of Captiva rentals varies greatly. On the lower end, you can find budget-friendly options like condos or apartments starting around $250. However, if you’re looking for something a bit more upscale Captiva Island house rentals, like a luxury beachfront villa for a group, nightly prices can range from $500 up to $2,500 or more.

  • How many Captiva Island vacation rentals are available?

    It may be a small island, but there are hundreds of vacation rentals on Captiva Island including private homes, oceanfront condos, and bayside villas all equipped with modern amenities for the ultimate beach vacation.