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House vacation rentals in Gasparilla Island

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Top-rated house rentals in Gasparilla Island

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Four beach chairs with vibrant tropical patterns are positioned on sandy shore, facing the sparkling Gulf waters. The bright sunlight reflects off the water's surface, creating a serene coastal scene perfect for relaxation.

Home in Englewood

5 out of 5 average rating, 38 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Located right on the Gulf, our renovated beach cottage is equipped with everything you need for a relaxing getaway. With private beach access and outdoor dining area, take in the views and enjoy with your family, friends or a solo trip to reset with a little R&R. This 2-bedroom, 2-bath bungalow has all the accoutrements for your a home-away-from-home, complete with beach chairs, boogie boards, beach games and of course, sun tan lotion. Come for some fun in the sun, your beachfront oasis awaits!

Top guest favorite

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Cape Coral

4.99 out of 5 average rating, 225 reviews

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Top guest favorite

An inviting heated saltwater pool is framed by swaying palm trees and lush greenery, offering serene views of a freshwater canal. Two lounge chairs are positioned in the shallows of the pool, creating a perfect spot for relaxation under the clear blue sky.

Home in Cape Coral

4.97 out of 5 average rating, 58 reviews

New Gorgeous Smart Home with Heated Pool on the Ca

Unwind in style in this spacious and modern home. Here's what awaits you: Smart Home Technology: Control lights, temperature, and even the front door with voice commands or your smartphone for a seamless experience. Heated Saltwater Pool: Take a refreshing dip in the sparkling pool, perfect for year-round enjoyment. Dedicated Workout Area: Maintain your fitness routine with a private space equipped for exercise. Freshwater Canal Views: Wake up to calming water views and the sounds of nature.

Top guest favorite

A well-maintained outdoor space features a private mini golf course with three putting greens and surrounding palm trees. The Key West-style home is visible in the background against a clear blue sky, with neatly trimmed landscaping and a fenced yard enhancing the tranquil setting.

Home in Placida

5 out of 5 average rating, 12 reviews

Seaside Boca (Pool + Sauna + Mini Golf + Spa)

Have fun with the whole family at this stylish new Airbnb. With its Key West vibes you’ll be sure to have a great time here! Boca Grande is just minutes away, Publix and shopping center are a short bike ride and boats are welcome as the marina is right next door. House is located in the tranquil area of Cape Haze close to Golf courses where you can stroll or bike to you hearts content. We just added a Game Room, a Pool with jacuzzi, Sauna, plus a multi court and Mini Golf (pics jus refreshed)

The kitchen features light wood cabinetry and stainless steel appliances, complemented by a spacious dining table set against a backdrop of large windows that allow natural light and views of the lush greenery outside.

Home in Boca Grande

4.86 out of 5 average rating, 36 reviews

Island Oasis- Boca Grande Club

We beat Milton and are ready to host you. The Village Houses in the Boca Grande Club possess a distinct charm that sets them apart. The village houses offer an intimate connection to nature. Our homes is surrounded by lush tropical foliage, providing a serene backdrop of swaying palms and vibrant flowers. Our guests enjoy access to a range of exclusive amenities. Whether lounging by the pool, or indulging in gourmet dining, out home provides a wealth of experiences for our guests.

Top guest favorite

A vibrant blue exterior of the home is showcased, framed by tall palm trees under a partly cloudy sky. A spacious driveway is visible, providing ample parking space in front of the house, which features a welcoming façade with multiple windows.

Home in Englewood

4.98 out of 5 average rating, 130 reviews

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!

Luxury Prime Island Location-Enjoy the best location on the island with our family & pet-friendly home (pets require approval & $125/pet fee). Just steps from our private beach & 1 mile from bars and restaurants, with a free shuttle service to beaches, dining, & nightlife. Relax in comfort w/ soft beds, a spacious couch, and flat-screen smart TVs in every room & fast WiFi. We offer bikes and beach equipment. 1 mile from Manasota Key public beach. Book now for the ultimate island retreat!

Top guest favorite

A contemporary dining area features a round table set for four, surrounded by sleek chairs. Large glass walls provide abundant natural light, revealing views of the outdoor space. A modern chandelier hangs above, adding an elegant touch to the inviting atmosphere.

Home in Rotonda West

5 out of 5 average rating, 5 reviews

Turtle Bay - minutes to Boca Grande!

Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

Top guest favorite

A weathered driftwood log is positioned on a sandy beach, with calm waves gently lapping at its base. The sky above is filled with soft hues of orange and pink, suggesting a sunset. A person sits on the log, gazing at the horizon.

Home in Placida

5 out of 5 average rating, 34 reviews

Salty Mermaid on Little Gasparilla Island/LGI

Charming beach house on Little Gasparilla Island (LGI) The Salty Mermaid offers a unique tropical paradise on a private barrier Island, with 7 miles of undisturbed white sandy beaches. Embrace the old Florida island vibe. Enchanted island steeped in pirate lore, legend has it, the spanish pirate Jose Gaspar, nicknamed Gasparilla, made this beautiful island his secret base hideaway. Local legends whisper of buried treasures hidden beneath the islands sandy shores. Come get Salty!

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

4.95 out of 5 average rating, 129 reviews

Steps To Private Beach Captiva Includes Golfcart

LABOR DAY SPECIALS Golf Cart and Club Membership Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories!

Top guest favorite

A spacious patio area is showcased, featuring a comfortable sectional sofa adorned with colorful pillows. A coffee table is positioned in front, while the heated pool and a wooden pergola are visible through large screened windows, enhancing the outdoor experience.

Home in Englewood

4.99 out of 5 average rating, 102 reviews

Green Bamboo - saltwater pool, great backyard.

Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

Top guest favorite

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

Home in Cape Coral

4.97 out of 5 average rating, 115 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

An aerial view captures a spacious outdoor area featuring a heated saltwater pool bordered by lounge chairs and wooden furniture. Lush palm trees and plants surround the patio, while a vibrant yellow house provides a cheerful backdrop.

Home in Englewood

4.92 out of 5 average rating, 143 reviews

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Gasparilla Island house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A serene pool area is showcased, featuring a clear blue pool surrounded by a spacious patio. Tropical plants create a lush backdrop, with seating options available under the bright sky. The setting offers a blend of relaxation and natural beauty in a tropical oasis.

Home in Bokeelia

4.86 out of 5 average rating, 35 reviews

Paradise Found! - 3/2 Pool Home

Top guest favorite

An inviting screened-in patio features a large heated swimming pool surrounded by lounge chairs. Sculptures adorn the sides of the pool, and lush greenery is visible through the expansive windows, offering tranquil views of the outdoors and tranquil ambiance.

Home in Cape Coral

5 out of 5 average rating, 70 reviews

Luxe Riverfront Retreat~Pool~Spa~Bar~Tropical Yard

Top guest favorite

A contemporary two-story home is depicted overlooking a serene pond. A fountain creates gentle ripples on the water's surface, while palm trees and lush greenery frame the scene, contributing to an inviting outdoor setting.

Home in Placida

5 out of 5 average rating, 13 reviews

Sea La Vie

Top guest favorite

The inviting outdoor area features a heated saltwater pool with an integrated whirlpool. Sun loungers are positioned nearby, and the screened enclosure creates a bright, airy atmosphere with views of the surrounding greenery and water.

Home in Cape Coral

5 out of 5 average rating, 16 reviews

Brandnew Villa - pool & spa at canal south facing

A private pool area is surrounded by a screened enclosure, featuring a refreshing salt-water pool. Two loungers are positioned for relaxation, with a small table and chairs visible in the background, providing a space for outdoor leisure and enjoyment.

Home in Rotonda West

4.94 out of 5 average rating, 126 reviews

Waterfront Villa Shellflower with private pool

Top guest favorite

The front of the home is framed by several palm trees and succulent plants, providing a tropical ambiance. A well-maintained lawn is visible, leading up to the entrance, which features a modern design with large windows and a covered porch.

Home in Rotonda West

5 out of 5 average rating, 28 reviews

Beautiful Floridian Oasis

An inviting pool area is enclosed by a screened lanai, allowing for unobstructed views of a colorful sunset. The clear water reflects the warm hues of the sky, while the surrounding pavers enhance the serene atmosphere of the outdoor space.

Home in Rotonda West

5 out of 5 average rating, 13 reviews

Upscale Getaway

Top guest favorite

An inviting outdoor area features a heated lap pool with a dolphin fountain, surrounded by palm trees and a protective screen enclosure. Lounge chairs are positioned nearby, overlooking the canal and providing a serene water view.

Home in Punta Gorda

5 out of 5 average rating, 37 reviews

Luxury long waterview w/pool-kayaks-clubs-bikes!

Weekly house rentals

The beachfront cottage is surrounded by lush foliage, showcasing a two-story structure with a metal roof and large windows. Soft light spills from the interior, highlighting a welcoming atmosphere. A wooden walkway leads to the entrance, inviting guests to explore the natural surroundings.

Home in Placida

4.88 out of 5 average rating, 26 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

Top guest favorite

The exterior of a remodeled home is framed by soft sunset hues, revealing a welcoming entrance with large windows. A landscaped lawn features low-maintenance plants along the pathway leading to the front door, complemented by a spacious driveway and garage.

Home in Rotonda West

4.97 out of 5 average rating, 29 reviews

Luxury Retreat: Oasis with Pool & Putting Green.

An outdoor seating area features a wooden picnic table and bright green plastic chairs, overlooking the sandy beach and ocean. A hammock hangs gently between posts, providing a relaxing space. Light filters through the open structure, creating a serene ambiance.

Home in Captiva

5 out of 5 average rating, 16 reviews

Windows on the Water "W.O.W."

Top guest favorite

The image captures a scenic view of Lemon Bay at sunset, with vibrant colors reflecting on the water. Two palm trees stand in the foreground, while a dock with hoists is visible along the shoreline, providing access to boating activities.

Home in Englewood

5 out of 5 average rating, 14 reviews

Lemon Bay Retreat-Boat/Jet Ski Hoist!

Top guest favorite

A well-maintained exterior of a villa features a neatly landscaped front yard with green grass and a planted palm tree. The building showcases a combination of white walls and reddish roof tiles, with a front door framed by bright lighting.

Home in Port Charlotte

5 out of 5 average rating, 26 reviews

Lake Marlin Villa 2

Top guest favorite

A charming bayfront house with a vibrant blue exterior is depicted. A spacious deck with white railings is accessed by a set of outdoor stairs. Tropical greenery surrounds the home, while colorful murals are painted on the walls, adding character to the inviting entrance.

Home in Placida

5 out of 5 average rating, 5 reviews

Poseiden House on Little Gasparilla Is

Top guest favorite

A scenic view of the canal-side property showcasing a wooden dock with a boat lift, surrounded by lush tropical vegetation. Sun loungers are placed on a manicured lawn, and the house's screened-in porch is visible, highlighting the tranquil waterfront setting.

Home in Bokeelia

5 out of 5 average rating, 30 reviews

Waterfront Oasis with Boat Lift & Hot Tub

The living area showcases a spacious sectional sofa adorned with decorative pillows. A 65-inch smart TV is mounted on the wall, while large windows allow natural light to fill the room. A dining area with modern lighting and a fully equipped kitchen can be seen in the background.

Home in Rotonda West

4.9 out of 5 average rating, 20 reviews

AquaMarineVilla/Spa/beaches/luxury/BocaGrande/new

Private house rentals

A bright and airy sitting area is presented with a view of the beach through expansive screened windows. Comfortable seating includes two chairs and a table, with soft colors enhancing the tranquil ambiance. The ceiling fan adds a cooling touch to the space.

Home in Sanibel

4.82 out of 5 average rating, 33 reviews

Premier Beachfront Residence at Villa Sanibel

A screened-in outdoor space features a heated saltwater pool surrounded by lounge chairs. Dining area is visible with a large table set for gatherings. Sunlight reflects off the water, creating a bright atmosphere. A waterway can be seen in the background, enhancing the serene environment.

Home in Rotonda West

5 out of 5 average rating, 8 reviews

Tropical Oasis, pool, pelaton, golf, dog friendly

The beach house stands prominently against a vibrant sunset sky, showcasing its welcoming façade. A sandy path leads through lush landscaping, guiding the eye toward the tranquil waters in the background. The scene radiates an inviting coastal charm, melding structure and nature.

Home in Placida

4.95 out of 5 average rating, 42 reviews

CocoHut

A curved swimming pool is set against a backdrop of lush tropical foliage and palm trees, with water views extending to a nearby dock. Brightly colored pots with plants are placed around the pool area, enhancing the serene outdoor setting.

Home in Sarasota

4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

A cozy nook is observed with two upholstered chairs, one adorned with a blue cushion, facing large windows. The sunset casts warm hues, providing a scenic view of palm trees and the beach, while a small decorative stool is placed between the chairs.

Home in Englewood

4.92 out of 5 average rating, 25 reviews

Sun-Soaked Beach House

The exterior of the beach house is showcased, featuring a covered porch with wooden railings and an American flag. Tropical palm trees surround the property, and stairs lead to the elevated entrance, highlighting the inviting design and island charm.

Home in Captiva

4.92 out of 5 average rating, 24 reviews

2/2 SandDollars, CLUB, Boat Slip

Top guest favorite

A pathway lined with palm trees leads toward a private area overlooking the Gulf of Mexico. A wooden fence and a utility structure are visible, with a pebbled surface providing texture. The turquoise waters are situated in the background against a clear blue sky.

Home in Englewood

5 out of 5 average rating, 15 reviews

Manasota Key to Relaxation

Top guest favorite

A private pool area features a heated pool and spa, surrounded by a screened enclosure. The serene outdoor space includes textured stone decking and seating, while lush greenery frames the view. Panoramic sliding doors lead into an inviting interior living space.

Home in Placida

4.93 out of 5 average rating, 29 reviews

AMAZING Cape Haze Location -community kayak launch

Destinations to explore