
Holiday rentals with a pool in Gasparilla Island
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Top-rated rentals with a pool in Gasparilla Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Sunset Retreat - Private Pool Near Gulf Beaches
Escape to Rotonda West! This brand-new, canal-front home offers 5 beds + study, 2.5 baths, reinforced safe room, and private pool, patio screen, perfect for privacy &relaxing. Enjoy a modern kitchen with quartz, high ceilings, and a spacious patio overlooking canals; great fishing. TVs, indoor and outdoor games and toys. Just 10 mins from stunning beaches and breathtaking sunsets. Conveniently located near 5 golf courses, pickleball, shops, & restaurants. Beach items provided! Florida paradise!

Beach Chalet Gulf View
Experience the ultimate beach vacation in our stunning beachfront condo, located on the Gulf of Mexico. It offers breathtaking ocean views and direct access to pristine sandy beaches. The condo sleeps four and offers one bedroom with a king size bed with a private attached bathroom. It also has a queen size murphy bed and an additional full bathroom. The modern kitchen is fully equipped with all the essentials. Plus, the resort offers an onsite pool, fitness center, tennis courts & restaurant.

Seaside Villa Majestic
Welcome to our beautiful and modern Seaside Villa Majestic, which was built in 2012 and completely renovated in 2019. Thereby not only all floors were renewed but also the kitchen was replaced. In 2023 the Seaside Villa Majestic was repainted inside and out. The villa has a perfect location in the Rosegarden area overlooking a wide canal. In just a few minutes you can reach the open river by boat. From the pool area the great location is further enhanced by the large heated infinity pool.

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.

Peaceful waterfront home
Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Condo in Four Winds! 2/2 Incredible Water Views!
This condo offers the finest in island getaway accommodations. Beautiful waterfront 2 bedroom/2 bath unit with abundant amenities to round out a relaxing boating and fishing vacation experience. Unit 302 has a screened-in lanai and a water view. It is beautifully appointed with a complete kitchen, washer/dryer, wi-fi, cable television, 48 state free long distance, boat docks, and a swimming pool on site. This condo building has an elevator for easier access.

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.

Private Heated Pool + Swim-Up Bar • Mins to Beach
Unwind in this thoughtfully designed 3-bedroom Florida retreat just 5 miles from Englewood Beach. Enjoy a private, heated pool with swim-up bar, screened lanai, and lush tropical privacy. Inside, you’ll find an open-concept living space, fully equipped kitchen, spa-style primary suite, and comfortable guest rooms. Ideal for families, couples, or friends seeking comfort, privacy, and easy access to beaches, golf, and dining.

New Villa Alhambra Lake at the lake-gameroom-dock
Brand new villa with heated infinity pool, spa/whirlpool and low-water area in waterfront south-facing orientation including fantastic views over Lake Alhambra for sole use. Modern and tastefully furnished villa in an absolutely quiet cul-de-sac. The concept and focus of the house are on the unique lake and the extremely spacious outdoor area, which invites you to relax, linger and recharge your batteries. New Gameroom

Last Minute-Villa Regency, luxury villa, pool, spa
This awesome villa has almost 3300 sqft of living space and offers the Florida charme - par excellence. The villa is located on a wide canal with gulf access in the beautiful south-west of Cape Coral. The south-west facing position of this house will guarantee plenty of sun all day long and the gorgeous Florida sunsets with nature views over the mangroves.

Luxury Villa: Pool, Hot Tub And Amazing Lake View
Escape to a private waterfront paradise on the famous Eight Lakes! This luxurious home offers spectacular sunset views from your private infinity pool and hot tub. Perfect for a relaxing retreat, it features seamless indoor-outdoor living, a gourmet kitchen, and high-end amenities. Ideal for couples or small groups seeking an unforgettable getaway.

Oz Cottage 2.9 m beach
The Oz Cottage room apartment is funky with all kinds off nooks and crannies! Walking distance to Lemon bay for beautiful sunsets. Great restaurants with outdoor dining and music on Dearborn St. Tennis courts, wonderful Library and a nice park are all within walking distance. 2.9 miles to Englewood Beach
Popular amenities for Gasparilla Island rentals with a pool
House rentals with a pool

Tropical Oasis, pool, golf, dog friendly

Waterfront Villa Shellflower with private pool

Relaxing Poolside Retreat

Surfside Elegance SW Cape Coral Luxe Vacation home

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

NEW BUILD -Heated Pool & Spa- Lake - West Exposure

Cape Coral Paradise Villa W/ Heated Saltwater Pool

Our Goal: Your Best Stay Yet!
Apartment rentals with a pool

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

Sunset Beach

Rare walkout condo on Sanibel beach

Entire Beachside Condo! Don’t worry Beach Happy!

South Seas Resort Beach Villa 🌴 On The Beach !

Gulf Water Views + 2 bikes, beach gear weekly stay

On the Beach; Siesta Key SunBum Studio

Near beach. Pool view. King bed. Daily rentals
Other holiday rentals with a pool

Luxury Waterfront Home • Pool • Dock • Near Beach

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Sho Me Sunshine - Lake Front w/ Southern Exposure

Sanibel Harbour Resort - 614: Water views

Palm View - Boat Dock and Tropical Lanai Space

Golden Globe - luxury on the canal with pool/spa

Boardwalk Beachfront Getaway

Paradise Palms | Private Pool | 10 min to Beach
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
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- House rentals Gasparilla Island
- Family-friendly rentals Gasparilla Island
- Rentals with a washing machine and dryer Gasparilla Island
- Rentals with beach access Gasparilla Island
- Rentals with outdoor seating Gasparilla Island
- Rentals with a patio Gasparilla Island
- Rentals with pools Florida
- Rentals with pools United States
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Lido Key Beach
- Caspersen Beach
- Manasota Key Beach
- Lovers Key Beach
- Englewood Beach
- Lakewood National Golf Club
- Myakka River State Park
- Stump Pass Beach State Park
- Clam Pass Park
- Bonita National Golf & Country Club
- Marie Selby Botanical Gardens
- Heritage Bay Golf & Country Club
- Blind Pass Beach
- North Jetty Beach
- South Jetty Beach
- Edison & Ford Winter Estates
- Tara Golf & Country Club
- Esplanade Golf & Country Club of Naples
- Florida Gulf Coast University
- Boca Grande Pass




