
Holiday rentals with a pool in Little Gasparilla Island
Find and book unique homes with a pool on Airbnb
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.

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.

Sunset Beach Cottage South
Spectacular panoramic views in your private 4 bed/4 bath home on a pristine 7 mile sugar sand beach. 2 master bedrooms w/private baths & balconies overlooking the ocean. Fully stocked kitchen. 2 kayaks are provided. Between the beach, pool, and lagoon you will be in paradise. Palm Island is a 3 minute car ferry ride or personal boat, which ensures a relaxing and tropical getaway. Incredible wildlife & shells galore. There is a restaurant on the island along w/a gift shop & convenience store.

Gulf Front Escape + Beach Access, Pet Friendly
🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

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.

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.

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.

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.

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)

Lux Home on Gulf w/Private POOL & 50ft 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!

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, full sofa bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach. Close to everything!!

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)

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.
Popular amenities for Little Gasparilla Island rentals with a pool
House rentals with a pool

Suite Sun

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Sunset Retreat - Private Pool Near Gulf Beaches

Luxury Golf Villa w/ Heated Pool & Spa

Sun & Sand Spacious Vacation Canal Pool House

Lemon Bay Getaway

Heated Pool• Pool Table•2 King Beds•BBQ•Fast WiFi

Heated Pool, Hot Tub, Fire Pit + RV/Boat Parking
Apartment rentals with a pool

On Manasota Key w direct access to our Beach! (A)

Burnt Store Marina- Harbor Towers, 2bdrm, GulfView

Location! Gulf Condo @ S. Jetty 30 day minimum

Vintage Villa, Thirty-Five

Spacious 2BR 2BA Beach Condo for Perfect Vacation

A little slice of paradise

Private Beach, Fishing Dock & Heated Pool Paradise

Burnt Store Marina- 2BR w/ pool, marina, gulf view
Other holiday rentals with a pool

New Modern Villa Beach 10 Min Heated Pool Luxury

Pool Oasis Getaway Near the Beach ~ Canal View

Venice Beach Villa/walk to beach/swimspa-pool

Peaceful waterfront home

Englewood Beach Villa - 3 min Walk to the Beach!

Private Heated Pool + Swim-Up Bar • Mins to Beach

Tropical Bliss | Lush Garden Poolside Retreat

Hello Summer, full refund*, pool heat, sleeps 6
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Rentals with lake access Little Gasparilla Island
- Rentals with a hot tub Little Gasparilla Island
- Rentals with beach access Little Gasparilla Island
- Rentals with a washing machine and dryer Little Gasparilla Island
- Beachfront rentals Little Gasparilla Island
- Pet-friendly rentals Little Gasparilla Island
- Family-friendly rentals Little Gasparilla Island
- House rentals Little Gasparilla Island
- Rentals with a kayak Little Gasparilla Island
- Rentals with a fireplace Little Gasparilla Island
- Cottage rentals Little Gasparilla Island
- Fitness-friendly rentals Little Gasparilla Island
- Apartment rentals Little Gasparilla Island
- Villa rentals Little Gasparilla Island
- Rentals with outdoor seating Little Gasparilla Island
- Rentals with a firepit Little Gasparilla Island
- Waterfront rentals Little Gasparilla Island
- Flat rentals Little Gasparilla Island
- Rentals with a patio Little Gasparilla Island
- Rentals with pools Charlotte County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Coquina Beach
- Caspersen Beach
- Lido Key Beach
- Cortez Beach
- Anna Maria Public Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Lovers Key Beach
- Englewood Beach
- Myakka River State Park
- Lakewood National Golf Club
- Stump Pass Beach State Park
- Img Academy
- Marie Selby Botanical Gardens
- Blind Pass Beach
- Tara Golf & Country Club
- South Jetty Beach
- North Jetty Beach
- Edison & Ford Winter Estates




