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Waterfront vacation rentals in Little Gasparilla Island

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Little Gasparilla Island

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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

4.91 out of 5 average rating, 274 reviews

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.

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

Escape to 3 acres of tropical bliss on exclusive Palm Island, where luxury meets seclusion. This beautifully updated 5-bedroom, 4-bathroom retreat offers breathtaking views of a serene pond and the Gulf of America. Heated pool & jacuzzi, 50-ft private boat dock, Home theater & game room, Kayaks, bikes, pool table, ping pong, and more, Fire pit, basketball court, volleyball, Steps from a private beach. Accessible only by private ferry, this is more than a getaway; it’s your slice of paradise.

The house is surrounded by lush greenery, featuring a large screened porch that offers shaded outdoor seating. A pool table is visible on the deck, which showcases a wooden railing and overlooks the landscape. A metal roof reflects the sunlight, enhancing the home's serene atmosphere.

Home in Placida

4.9 out of 5 average rating, 42 reviews

Coconut Paradise POOL! Little Gasparilla Island

Just Ask!! Beach pics since storms. All cCleaned up! House is 100% and Beautiful! Relax with the whole family at this peaceful place to stay on Little Gasparilla Island! Newer Pool Home! Fast STARLINK Internet!! Heated pool/Hot tub. Private beach access and dock access. Boat Access only. Take the private water taxi across the bay to a true island paradise. Or bring your own boat! Boats must be 24’ of less. Over 50 coconut palms. Pool table, kayaks, house fully stocked!

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

4.95 out of 5 average rating, 42 reviews

CocoHut

CocoHut has a private beach on a secluded barrier island; accessible only by boat to owners+guests. 2 vacant lots to the south & vegetation to the north, mean there is absolutely no overlook from neighbors. It’s THE ultimate spa for your soul! Look out onto the sea shimmering in the sun; commune with the clouds crossing a canvas of blue; soak in sunsets & gaze at a galaxy full of stars, free from light pollution. Choose 1 or all, just know you'll relax & refresh your body & soul.

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!

Welcome to the most secluded spot on Little Gasparilla Island! Our Beach Cottage property is on the beach with all-natural surroundings: a state park, a mangrove lagoon, and the Gulf of Mexico. It boasts front views of the water and gorgeous island sunsets year-round. You'll have boat space on our private dock and amenities including kayaks, paddle boards, an outdoor bayside dining area, coffee bar with complimentary coffee, private grilling area, fire pit, and much more!

Top guest favorite

A stylish pool area is illuminated by soft lighting at night, featuring two large red umbrellas over submerged seating. Calm waters reflect the surroundings, while palm trees frame the view, creating a serene atmosphere by the water's edge.

Home in Port Charlotte

4.95 out of 5 average rating, 57 reviews

Amazing Peace River Views

House is a 2 bed, 2 bath layout. The Master bed is a king bed and the guest bedroom is a queen. Both bedrooms have walks in closets with easy and convenient shelving and built in hampers. The laundry is stocked with liquid soap and fragrance free powder with fast efficient machines. There are speakers in the house, lanai and pergola. You will be able to control them via your phone. There is a desk work area with extra monitor for laptops and a printer for your use.

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

4.88 out of 5 average rating, 198 reviews

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.

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

4.94 out of 5 average rating, 126 reviews

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.

A spacious screened porch features comfortable seating arrangements with a wooden table at the center. Inviting ocean views are visible through the mesh screens, alongside swaying palms. Decorative throw pillows enhance the cozy feel, and soft lighting is provided by string lights overhead.

Home in Placida

5 out of 5 average rating, 8 reviews

"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.

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

4.97 out of 5 average rating, 333 reviews

NEW 4/NTS AUG 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!

Top guest favorite

Home in Rotonda West

5 out of 5 average rating, 70 reviews

Family-Friendly Oasis |Pool, Beaches, Pet Friendly

Welcome to The Coastal Coconut 🥥, your private Florida retreat with a outdoor pool, pool table, and all the beach gear you need. Perfect for families, groups, or couples looking to relax, explore, and create unforgettable Gulf Coast memories. Spend the day shelling at nearby beaches, challenge friends to a game of pool, then grill by the fire table as the sun sets.

The home showcases a classic beach house design with a light green facade and a spacious deck. Multiple seating areas, including orange Adirondack chairs, are arranged on the lower level. Stairs lead up to a covered upper deck, providing an inviting outdoor space with views of the surrounding nature.

Home in Placida

4.78 out of 5 average rating, 37 reviews

3/2 LGI Gulf Front w/Dock

Gulf of America Beachfront Island Home is a perfect getaway! Enjoy the beach in your front yard and dock your boat on the bay! This three-bed, 2 bath gulf front home has an open floor plan with multiple dining areas both indoor and outdoor. Pocket sliders can be opened to extend the living space and hear the sound of the waves while you sip your morning coffee.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Little Gasparilla Island waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

A waterfront view showcases colorful buildings surrounded by palm trees. Small boats are docked at a wooden pier extending into the calm water, reflecting the vibrant scenery. Lush greenery complements the tropical atmosphere, creating a serene and inviting environment.

Apartment in Matlacha

4.62 out of 5 average rating, 140 reviews

Grouper Room in Matlacha * Redfish is open!

Top guest favorite

An aerial view captures a waterfront community along the Myakka River. The image highlights the blue rooftop condos nestled among lush greenery, with a serene water expanse stretching into the horizon. The area is marked by a wooden pier extending into the river.

Apartment in Port Charlotte

4.9 out of 5 average rating, 10 reviews

Waterfront Condo w Scenic Views-Heated Pool

An enclosed swimming pool area features a spacious pool illuminated by soft lighting. Sun loungers are positioned around the pool, with a tranquil ambiance created by the twilight sky visible through the mesh. The landscaped yard offers a serene setting for relaxation.

Apartment in Englewood

4.94 out of 5 average rating, 16 reviews

CLEAN*Great Location*Dockage Available*HEATED Pool

A bright living area is featured, showcasing comfortable seating arranged around a wooden coffee table. A large wall art piece depicting ocean waves complements the decor. A ceiling fan and natural light enhance the space, while potted plants add a touch of greenery.

Apartment in Englewood

4.89 out of 5 average rating, 46 reviews

Turtle Bay 1A Island Condo

Top guest favorite

A resort-style pool area is surrounded by palm trees, featuring a spacious pool and a hot tub. Lounge chairs are placed around the pool deck, with a covered seating area visible in the background. Clear blue skies enhance the inviting atmosphere.

Apartment in Cape Haze

5 out of 5 average rating, 6 reviews

Marina front, pool, beach condo!

A spacious pool area is enclosed with a screened enclosure, featuring a clear blue pool and lounging spaces. Outdoor seating is arranged near the water, while a dining set is positioned under the shade. Lush greenery can be seen beyond the pool area.

Apartment in Port Charlotte

4.78 out of 5 average rating, 64 reviews

Luxury Suite ~ Heated Pool ~ Private Entrance

A spacious living area is highlighted by comfortable leather seating arranged around a round coffee table. Sunlight filters through large sliding glass doors, leading to a private balcony with views of the beach. A flat-screen TV is mounted against a soothing blue sideboard.

Apartment in Englewood

5 out of 5 average rating, 3 reviews

The Palms – 3BR Gulffront, Sand & Sunsets

A bright and airy room features a spacious bed adorned with decorative pillows. A large window allows ample natural light and offers a view of the waterfront. Light-colored walls and furnishings create an inviting ambiance, enhancing the serene atmosphere of the space.

Apartment in Cape Coral

4.94 out of 5 average rating, 155 reviews

Suite with lake view.

Waterfront house rentals

Top guest favorite

A modern waterfront home is depicted, featuring a light-colored facade and a three-car garage. A paver driveway leads to the entrance, surrounded by manicured grass and a few ornamental shrubs. The sky is bright with scattered clouds, enhancing the home's welcoming appearance.

Home in Cape Coral

5 out of 5 average rating, 6 reviews

Coral Coast Retreat

An aerial view captures a coastal home surrounded by lush greenery, positioned near a sandy beach. The ocean's horizon meets the evening sky, showcasing soft hues as the sun sets. The home's design features multiple windows, reflecting the serene outdoor environment.

Home in Englewood

4.77 out of 5 average rating, 13 reviews

Private Beach & Incredible Sunsets-Exquisite Home

A serene outdoor space features a heated pool surrounded by a screened enclosure. Lush greenery lines the edge of the saltwater canal, providing a tranquil backdrop under a clear blue sky.

Home in Port Charlotte

5 out of 5 average rating, 12 reviews

Waterfront Key West Style Home, Heated Pool

Top guest favorite

A screened-in pool area features a clear blue pool surrounded by a spacious deck. Lush greenery and trees are visible through the screens, and the sky is adorned with soft hues of orange and pink, signaling sunset.

Home in Rotonda West

4.95 out of 5 average rating, 65 reviews

Spacious Vacation Home

Top guest favorite

A tranquil pool area is highlighted by a heated lap pool with a dolphin fountain, surrounded by lush coconut palms. The water view captures a serene canal lined with boats and docks, framed by a screened enclosure that invites natural sunlight.

Home in Punta Gorda

5 out of 5 average rating, 37 reviews

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

An open-concept living area features modern furnishings, including a spacious sectional and a unique wooden coffee table. Natural light fills the room through large sliding glass doors that lead to an outdoor view. A tasteful area rug anchors the space, complementing the elegant decor.

Home in Cape Coral

5 out of 5 average rating, 5 reviews

Modern Luxury Oasis w/ Pool and Dock

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

A modern single-story home is displayed, featuring an elegant façade and a spacious driveway lined with paver stones. The entryway is framed by lush landscaping, and the three-garage doors provide ample parking. A clear blue sky highlights the attractive exterior design.

Home in Rotonda West

4.71 out of 5 average rating, 7 reviews

Rotonda River Villa pool home #1125

Waterfront condo rentals

Top guest favorite

A screened-in lanai features comfortable patio furniture, including two chairs and a round table, arranged on a decorative rug. The expansive glass doors frame a view of the marina, with docks lined by boats and a clear blue sky in the background.

Condo in Punta Gorda

4.95 out of 5 average rating, 61 reviews

One bedroom condo - overlooking harbor!

A covered outdoor patio features a rectangular table surrounded by six black chairs. Palm trees and the tranquil waters of Lemon Bay are visible in the background, providing a scenic view. The spacious area is ideal for relaxation and dining.

Condo in Englewood

4.95 out of 5 average rating, 21 reviews

Bay Breeze @ManasotaKeyCondos

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

4.79 out of 5 average rating, 131 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

Top guest favorite

An updated kitchen features sleek white cabinetry and modern stainless steel appliances. A spacious island provides additional counter space. Stylish lighting fixtures hang from the ceiling, while a decorative mirror and lamp enhance the room's design. Subtle textures and finishes add to the contemporary feel.

Condo in Venice

5 out of 5 average rating, 15 reviews

Location! Gulf Condo @ S. Jetty

A paved pathway lined with palm trees leads to the front of a single-story building. The structure features large windows, allowing natural light to illuminate the interior. Parking spaces are visible along the side, and the beachfront is seen in the distance.

Condo in Venice

4.93 out of 5 average rating, 54 reviews

Beachfront Venice Villas 1-bed Condo

A bright bedroom features a spacious bed with a yellow accent pillow and a knitted blanket draped over it. Two windows with blinds provide natural light, while wood beam ceilings add architectural interest. Nightstands flank the bed, and a small lamp offers additional lighting.

Condo in Englewood

5 out of 5 average rating, 7 reviews

Spot manatees from your balcony

Top guest favorite

A sandy path leads through lush green shrubs toward a beach house with a covered porch. The beach house's light exterior complements the cloudy sky, creating a serene coastal atmosphere. The surrounding foliage provides a natural frame for the view of the beach beyond.

Condo in Englewood

4.97 out of 5 average rating, 98 reviews

Studio, pool, private beach, boat dock shark teeth

The well-equipped kitchen features white cabinetry and stainless steel appliances, including a refrigerator and stove. A central island offers additional prep space. Natural light enters through a window above the sink, illuminating the neutral tile flooring.

Condo in Nokomis

4.86 out of 5 average rating, 50 reviews

Beachfront Getaway on Casey Key

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