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Holiday rentals with a pool in Little Gasparilla Island

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Top-rated rentals with a pool in Little Gasparilla Island

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Bungalow in Rotonda West
4.94 out of 5 average rating, 64 reviews

Heated Pool, Cozy 2 Bed-2 Bath House

Calm, quiet and safe neighbourhood close to many wonderful beaches,golf courses, bars and restaurants ! Enjoy the endless Floridian summer on the magnificent west coast, take part of a beach volleyball game or sit and enjoy the sun until sunset! 2 bathroom and 2 bedroom (1 king bed and 1 queen bed) pool house furnished with everything you need for an agreeable and comfortable stay. Private driveway, Fast wifi connection and work office available. Dishwasher, clothes washer and dryer on site.

Guest favourite
Condo in Englewood
4.79 out of 5 average rating, 141 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

BOOK HERE!!! STEPS TO WORLD FAMOUS Manasota Key BEACH, FREE PARKING. Private beach access. WALKING DISTANCE TO MANY RESTAURANTS. 2 Bedroom, 1 Bathroom, beach themed condo with HEATED POOL access across street. Complimentary grill and Gulf sunsets. Your morning coffee is on us! Beach chairs, towels, and sand toys supplied. Kitchen is updated with filtered water, ice, and utensils supplied. Master Bedroom has a queen sized bed, pull out drawers and fireplace. Boat dock slip available upon request.

Guest favourite
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, 281 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 favourite
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, 18 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.

Top Guest favourite
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, 9 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 favourite
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
4.94 out of 5 average rating, 31 reviews

AMAZING Cape Haze Location -community kayak launch

Ready for warm sunshine, tropical breezes and lush landscaping? Spaniard's Retreat is the ideal location for your get away. This home is set in the charming Old Florida neighborhood of Cape Haze. Old banyan and pin-oak trees line the picturesque streets where homes are spaciously placed. Upon entering you will be greeted by the panoramic sliding doors overlooking the heated pool and spa. This truly feels like a private oasis. 3 bedrooms and 2.5 baths offer generous accommodations.

Top Guest favourite
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, 114 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.

Superhost
An aerial view captures the condo complex nestled along the shoreline, bordered by lush greenery and water. The heated pool is visible, with a dock and boat slips extending into the bay. The tranquil ocean and beach are seen in the background under a clear blue sky.
Condo in Placida
4.89 out of 5 average rating, 36 reviews

LGI Hideaway- Includes golf cart & pool access!

"Florida's Best Beach". Views of the sunrise out the back screened-in porch overlooking the pond and amazing sunsets on the beach. Great amenities in the condo complex including free parking on the mainland, ferry, heated pool, and boat slip. Enjoy the sandy beaches by the provided golf cart! Please note: some other units nearby are currently under construction. Golf Cart provided at no additional cost and is operational (technician visits on Saturdays for any repairs needed)

Top Guest favourite
An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.
Home in Englewood
5 out of 5 average rating, 39 reviews

Lux Home on Gulf w/Private POOL & 100ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 100 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

Top Guest favourite
Condo in Placida
5 out of 5 average rating, 12 reviews

Beautiful Beaches at LGI Hideaway • Golf Cart

"Florida's Best Beach"! Newly remodeled. Fully stocked kitchen. Washer, dryer, smart TV. Lower storage area has items for a day at the beach- sand toys, tent, and beach chairs! Just bring your bathing suit, sandals and enjoy the paradise of Little Gasparilla Island! Please note: some other units nearby are currently under construction. Golf Cart provided at no additional cost and is operational (technician visits on Saturdays for any repairs needed)

Top Guest favourite
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
4.91 out of 5 average rating, 211 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.

Top Guest favourite
Condo in Englewood
4.97 out of 5 average rating, 104 reviews

Studio, pool, private beach, boat dock shark teeth

Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.

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