Vacation rentals in Gasparilla Island

4.98 out of 5 average rating, 102 reviews

An outdoor space features a screened-in pool area with a rectangular swimming pool and a hot tub. Poolside lounge chairs with blue cushions are arranged around a small table. Lush greenery is visible in the background, enhancing the private ambiance.

Villa in Cape Coral

LAST Minute! NEW Villa-Heated Saltwater Pool & Spa

Experience Cape Coral like never before all from this gorgeous 3bedroom, 3bath villa. This elegant villa boasts a vibrant interior decorated with Italian furniture and fully equipped kitchen. Begin your day with a few laps in the private pool before heading to the Yacht Club Public Beach, Sun Splash Family Waterpark or Pine Island to soak up some sun! After adventurous days, continue making memories back home with a family barbecue and a soak in the hot tub or have a movie night with loved ones!

4.91 out of 5 average rating, 271 reviews

A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.

Guesthouse in Englewood

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

4.89 out of 5 average rating, 146 reviews

An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.

Cottage in Englewood

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

4.96 out of 5 average rating, 127 reviews

An aerial view showcases a raised townhome surrounded by palm trees, with the beach and ocean visible in the background. The home's light blue exterior complements the coastal setting, while a spacious deck on the lower level offers an inviting space for relaxation.

Townhouse in Englewood

Summer Sunsets just 50 steps to uncrowded beach

Escape to your dream coastal retreat! This exquisite 2- king bedroom, 2-bathroom home is a paradise, located just steps from the beach. Nestled among swaying palm trees, this haven offers a serene oasis where the calming sounds of the water create a tranquil atmosphere for you and your loved ones. Live among palm trees, with the ocean as your neighbor and the sand as your playground. Natural light floods the modern interior through the large windows creating a warm and inviting atmosphere.

4.95 out of 5 average rating, 127 reviews

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

Steps To Private Beach Captiva Includes Golfcart

Relax and Reconnect at Our Charming 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 (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories!!

5 out of 5 average rating, 3 reviews

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

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!

4.88 out of 5 average rating, 197 reviews

A beachfront property is depicted, featuring a two-story structure with a spacious porch. Surrounding landscape includes sand and lush greenery, leading to the waves of the Gulf of Mexico. Sunbathers are seen in the distance, enjoying the beach atmosphere.

Condo in Englewood

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

4.98 out of 5 average rating, 125 reviews

A spacious living area is highlighted by a comfortable blue sofa and a glass-top coffee table, resting on a soft area rug. Exposed timber beams and stylish light fixtures create a warm ambiance. A spiral staircase leads to the upper level, while a modern kitchen is visible in the background.

Loft in Boca Grande

The Loft on Park Ave--Boca Grande FL

We survived the old 1-2 of Huricaines, Helene and Milton and are ready to host you! A unique loft in the heart of Boca Grande. Grab dinner and drinks and simply walk home. The loft apartment has great views of the main drag in Boca Grande. The timber framed interior and high end appliances assure you will have a comfortable stay. This is a great place to park your car-grab a golf cart- and enjoy the Boca Grande lifestyle.

4.94 out of 5 average rating, 115 reviews

An outdoor lanai features a swimming pool surrounded by a screened enclosure, providing a secure and open space. Comfortable seating arrangements are visible, with a decorative rug underfoot. Lush greenery can be seen beyond the pool area, enhancing the tranquil setting.

Home in Venice

Spacious 2 Bedroom Home | Near Beach | Heated Pool

This beautiful home just minutes from the beach offers 2 spacious king bedrooms, a queen sofa bed in the large open living area, and a full kitchen ready for entertaining. Gather your family around the dining room table for food and games and then relax on the lanai or have a float in the pool. The hosts provide Margaritaville frozen concoction machine, 2 bicycles, beach chairs, beach towels, shark tooth tools, and more.

4.94 out of 5 average rating, 124 reviews

A private aquatic area features a heated saltwater pool surrounded by a screened patio, offering views of the Rotonda River. Two blue chairs and a sun lounger are positioned nearby, creating a relaxing outdoor space. The pool steps are visible, inviting leisurely swims.

Home in Rotonda West

Waterfront Villa Shellflower with private pool

Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.

5 out of 5 average rating, 8 reviews

A dining area is positioned on a screened porch, featuring a wooden table surrounded by four chairs. A decorative bowl filled with shells rests on the table. Beyond the railing, scenic beach views and calm turquoise waters are visible, enhancing the space's relaxed atmosphere.

Home in Placida

"Salt of the Sea" - beachfront and pet friendly!

Brand New to the Rental Market! Experience the ultimate escape at "Salt of the Sea," a charming 1 bedroom/ 1 bathroom beachfront cottage located on the serene Little Gasparilla Island, a unique bridge-less barrier island. Here, you'll find no stores, no restaurants, no bars, and no cars – just pure relaxation and a chance to unplug from the hustle and bustle of everyday life.

4.97 out of 5 average rating, 330 reviews

A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.

Island in Sarasota

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Vacation rentals for every style

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Popular amenities for Gasparilla Island vacation rentals

Free parking on premises

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

Gasparilla Island beach vacation rentals

4.89 out of 5 average rating, 248 reviews

A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.

Condo in Sanibel

Rare walkout condo on Sanibel beach-Fully Restored

4.79 out of 5 average rating, 128 reviews

An aerial view captures the beachfront property surrounded by palm trees and lush greenery. The ocean is visible in the distance, framed by clear blue skies. A sandy path leads from the building to the beach, emphasizing the proximity to the water.

Condo in Englewood

Entire Beachside Condo! Don’t worry Beach Happy!

Condo in Fort Myers Beach

A private lanai overlooks the sandy beach and Gulf waters, featuring a small round table with a textured surface and two chairs. A bright pink pillow with the word 'Salty' adds a pop of colour, while distant beach umbrellas can be seen dotting the shore.

4.82 out of 5 average rating, 110 reviews

Oceanfront Views + Balcony Sunsets Bikes Included

4.95 out of 5 average rating, 21 reviews

A wooden boardwalk is lined with palm trees, leading towards a sandy beach and the Gulf. Lush greenery surrounds the pathway, with clear blue skies above, creating a welcoming atmosphere for a beach stroll.

Condo in Sanibel

"Seaspray" - beachfront, Amazing GULF VIEWS!

4.92 out of 5 average rating, 12 reviews

An outdoor pool area features a spacious infinity pool with clear water, surrounded by lounge chairs and an umbrella. The backdrop highlights the scenic canal, while palm trees sway gently under a bright blue sky, contributing to a relaxing atmosphere.

Villa in Cape Coral

Villa Sunset Beach – Heated Pool+Spa | Gulf Access

4.97 out of 5 average rating, 326 reviews

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

Condo in Siesta Key

On the Beach; Siesta Key SunBum Studio

4.93 out of 5 average rating, 146 reviews

A view from the porch captures a vibrant sunset over the Gulf of Mexico, with silhouettes of palm trees and nearby buildings. The warm colors of the sky blend into the horizon, creating a serene backdrop that enhances the coastal atmosphere.

Condo in Englewood

Gulf Side Condo Englewood Florida

4.95 out of 5 average rating, 42 reviews

A spacious dining area is set with a colorful tablecloth and comfortably accommodates multiple guests. The large windows offer unobstructed views of the ocean, allowing natural light to fill the room and creating a bright, inviting space.

Home in Placida

CocoHut

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Gasparilla Island house rentals

4.85 out of 5 average rating, 33 reviews

A comfortable living area features a dark leather sofa and colorful accent chairs. A coffee table is positioned centrally, with a television mounted on the wall. Large glass doors provide a view of the outdoor pool area, creating a bright and inviting space.

Home in Bokeelia

3/2 Pool Home - Paradise Found!

A heated pool with a clear blue surface is surrounded by a cozy patio area. Lounge chairs provide a space for relaxation, while lush palm trees and vibrant greenery frame the serene waterfront view. A shaded umbrella offers a spot to enjoy the outdoors.

4.98 out of 5 average rating, 124 reviews

Luxury Canal Villa: Heated Pool • Kayaks • Arcade

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.

5 out of 5 average rating, 16 reviews

Brandnew Villa - pool & spa at canal south facing

An outdoor seating area features a round wooden table with four matching chairs. A pool is visible in the background, along with a covered outdoor kitchen area and a flat-screen TV. The setting overlooks a canal, enhancing the relaxed atmosphere.

5 out of 5 average rating, 5 reviews

Havana Luxos - Luxury Vacation Rental Cape

4.96 out of 5 average rating, 69 reviews

A beach house with a two-story design is surrounded by lush greenery and palm trees. A driveway leads up to the property, which features large windows and a covered porch. A golf cart is parked in the foreground, enhancing the coastal appeal.

Home in Boca Grande

Perfect Beach House Excellent Location

4.92 out of 5 average rating, 13 reviews

An aerial view captures the waterfront property, highlighting the silver-roofed house surrounded by lush greenery and palm trees. A long wooden pier extends into the calm waters of Charlotte Harbor, inviting activities like fishing and kayaking.

Home in Bokeelia

The Harbor House

5 out of 5 average rating, 16 reviews

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

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

An expansive outdoor area features a massive infinity pool reflecting the colors of the sunset. Lounge chairs are positioned around the pool, while the villa’s modern architecture and wide glass doors provide a seamless connection to the inviting interior space.

5 out of 5 average rating, 6 reviews

Intervillas Florida - Villa Xanadu

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Beach house rentals in Gasparilla Island

4.77 out of 5 average rating, 35 reviews

The beachfront home is elevated, showcasing a spacious deck with seating areas. Lush greenery surrounds the property, while a sandy path leads to the beach. Large windows offer views of the outdoor space and invite natural light into the interior.

Home in Placida

3/2 LGI Gulf Front w/Dock

5 out of 5 average rating, 42 reviews

An aerial view showcases a charming beach town along the coastline, with the ocean's turquoise waters visible in the background. Several buildings with distinct architectural styles blend harmoniously, while palm trees punctuate the landscape, enhancing the coastal ambiance.

Home in Manasota Key

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

4.9 out of 5 average rating, 109 reviews

A shared outdoor area features a sparkling blue pool surrounded by lounge chairs. The building showcases a modern design with a light-colored facade and a wraparound deck for relaxation, complemented by palm trees and bright red umbrellas that add a pop of color.

Home in Siesta Key

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

5 out of 5 average rating, 36 reviews

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

"Lost Loon" Oceanfront Cottage by Roxy Rentals

4.86 out of 5 average rating, 102 reviews

A spacious living area features comfortable seating with neutral-toned sofas and an accent chair. A coffee table sits in the center, with decorative elements adding character. Natural light filters through large windows, enhancing the bright atmosphere, while pendant lights provide soft illumination.

Home in Bonita Springs

New Luxury Villa: 2 min walk to beach, gulf view

4.8 out of 5 average rating, 114 reviews

A vibrant outdoor area features a cozy splash pool surrounded by a stylish deck. Colorful pink lounge chairs are arranged nearby, and a large, eye-catching mural depicting marine life and a ship creates a captivating backdrop.

Home in Siesta Key

Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

4.84 out of 5 average rating, 170 reviews

An outdoor space features a shaded area with an umbrella and lounge chair, alongside an in-ground fire pit with seating for twelve. Soft sand surrounds the space, and lush greenery provides privacy. The sky is highlighted by vibrant sunset colors, creating a tranquil atmosphere.

Home in Fort Myers

Blue Beach Bungalow