
Holiday rentals with a pool in Gasparilla Island
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Top-rated rentals with a pool in Gasparilla Island
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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.

Boater’s Paradise-Stunning Sunsets! Games Room!
Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

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.

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.

Steps to Beach Captiva Includes CLUB & Golfcart
HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included 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(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

South Seas Resort Beach Villa 🌴 On The Beach !
South Seas Beach Villa 2527 is located directly on the beach. The beautiful sunsets over the Gulf of Mexico, along with the condo pool can be viewed from the private lanai. This updated unit has one king size bed located in the bedroom and pull out queen size sleeper sofa. The kitchen is fully stocked, there is an inside and outside dining table. You will have access to the beach, pool, pickleball, tennis courts, beach chairs & towels and BBQ grills located in the front of the unit.

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.

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!!

Island Home & Casita, Pool, Golf Cart, Beach
Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

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.

Island Getaway Pool-Ferry-Grocery Delivery Incl.
*FREE Island Grocery delivery/staging Enjoy our Locally Owned and Operated, Newly Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Gated Mainland Parking & Ferry to the Island incl. Walk the Uncrowded shelled beach with Birds, Dolphin and Manatee or Venture out for Prime Fishing & Kayaking SWFlorida has to Offer

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

Seashell Escape: Heated Pool•Golf Cart•Pool•Truste

Tropical Oasis, pool, golf, dog friendly

Sunset Retreat - Private Pool Near Gulf Beaches

2/2 SandDollars, CLUB, Boat Slip

Water view Villa private Heated Pool golf beach

Bokeelia Oasis! Heated Pool, Sleeps 12!

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games

Ultimate Luxury:Spa/Pool/Outdoor Kitchen/Firepits
Apartment rentals with a pool

Bay Breeze @ManasotaKeyCondos

Beachfront fully equipped apartment

Ocean Oasis on Manasota Key - Ocean View

Gulf Water Views + 2 bikes, beach gear weekly stay

Splendid Beach Villa Residence on Captiva

A little slice of paradise

Burnt Store Marina- 2BR w/ pool, marina, gulf view

Steps to Water! Beach to Bay, Penthouse!
Other holiday rentals with a pool

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Caper Beach Club Penthouse 2 - Gulf View

Florida, Cape Coral, SunShine

New Luxe Beachfrnt, Specatular Ocean Views + Club!

Heated Pool & Spa Family Villa

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

Secluded Paradise,Heated Pool,Beaches and Golf n.
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
- Rentals with a patio Gasparilla Island
- Rentals with outdoor seating Gasparilla Island
- Family-friendly rentals Gasparilla Island
- Rentals with a washing machine and dryer Gasparilla Island
- House rentals Gasparilla Island
- Rentals with beach access Gasparilla Island
- Rentals with pools Florida
- Rentals with pools United States
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Caspersen Beach
- Lido Key Beach
- Manasota Key Beach
- Lovers Key Beach
- Englewood Beach
- Myakka River State Park
- Lakewood National Golf Club
- Stump Pass Beach State Park
- Clam Pass Park
- Marie Selby Botanical Gardens
- Bonita National Golf & Country Club
- Heritage Bay Golf & Country Club
- Blind Pass Beach
- Tara Golf & Country Club
- Esplanade Golf & Country Club of Naples
- North Jetty Beach
- South Jetty Beach
- Edison & Ford Winter Estates
- Del Tura Golf & Country Club
- Boca Grande Pass




