A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

Hotels with Pool & Resorts in Gasparilla Island from AU$109

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Gasparilla Island Hotels with Pool

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Gasparilla Island hotels with a pool

An octagonal pool with a diving board, surrounded by lounge chairs and a small table.
A bedroom with a large bed, wooden headboard, bedside tables, a ceiling fan, and a wardrobe.
A bathroom with a marble sink, a toilet, a glass-enclosed shower, and bamboo-patterned walls.
A spacious indoor corridor with a central seating area, potted plants, and a high ceiling with skylights.

1. Boca Grande Hotel - King Room

Boca Grande Hotel - King Room
Boca Grande
  • Splash into poolside paradise at Boca Grande Hotel, near beaches, shopping, and dining.
AU$266
includes taxes & fees
4 Oct - 5 Oct
Boca Grande Hotel - King Room
An octagonal pool with a diving board, surrounded by lounge chairs and a small table.
A bathroom with a marble sink, a toilet, and a glass-enclosed shower.
A hotel room with two beds, a ceiling fan, and a large window with blinds.
A hotel entrance with a sign pointing to the office, palm trees, and a brick pathway.

2. Boca Grande Hotel - Queen Room

Boca Grande Hotel - Queen Room
Boca Grande
  • Family-friendly hotel offers relaxing getaway with shared pool and comfortable queen rooms.
AU$266
includes taxes & fees
4 Oct - 5 Oct
Boca Grande Hotel - Queen Room
An octagonal pool with a diving board, surrounded by lounge chairs and a small table.
A hotel entrance with a sign pointing to the office, palm trees, and a brick pathway.
A bedroom with a wooden dresser, a bed with a white quilt, and a door with a window.
A bathroom with a shower, toilet, and sink.

3. Boca Grande Hotel - Economy King Room

Boca Grande Hotel - Economy King Room
Boca Grande
AU$212
includes taxes & fees
4 Oct - 5 Oct
Boca Grande Hotel - Economy King Room
An octagonal pool with a diving board, surrounded by lounge chairs and a small table.
A hotel entrance with a sign pointing to the office, palm trees, and a brick pathway.
A bathroom with a shower, toilet, sink, and towel rack.
A hotel room with two wooden beds, a bedside table with a lamp, and a window with blinds.

4. Boca Grande Hotel - ADA Queen Room

Boca Grande Hotel - ADA Queen Room
Boca Grande
AU$285
includes taxes & fees
5 Oct - 6 Oct
Boca Grande Hotel - ADA Queen Room
A clear swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear sky.
A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.
A beach with thatched-roof structures, palm trees, and blue chairs.
A beach with a thatched-roof structure, palm trees, and a view of the sea.

5. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
Punta Gorda Isles
  • Sunlit days await at this bayside retreat with a sparkling pool, marina access, and vibrant shopping village just steps away.
AU$283
includes taxes & fees
30 Oct - 31 Oct
The Suites at Fishermen’s Village
A resort pool area with multiple sun loungers and umbrellas, surrounded by palm trees and a view of the ocean.
A beach with palm trees, string lights, and beach chairs.
A beachfront hotel with a central entrance, outdoor seating, and palm trees.
A restaurant with multiple tables and chairs, large windows with a view of the ocean, and hanging pendant lights.

6. South Seas

South Seas
Captiva
  • Waterfront resort offers 3 outdoor pools, waterpark with slides, and private beach access.
AU$517
includes taxes & fees
8 Oct - 9 Oct
South Seas
A resort with a central pool, multiple lounge areas, and a beach view.
A table set for dining with a view of the sunset over the ocean.
A covered porch with a view of the sea, a white railing, and two Adirondack chairs.
A balcony with a view of the beach, palm trees, and a clear sky.

7. Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa
Captiva
  • Discover a serene pool oasis with private beach access, where refreshing swims meet stunning sunsets over the bay.
AU$454
includes taxes & fees
12 Oct - 13 Oct
Tween Waters Island Resort & Spa
A swimming pool with a deck, lounge chairs, and a view of a river.
A compact kitchenette with a refrigerator, microwave, and coffee maker. There is a wooden table with two chairs and a mirror above it.
A hotel room with a large bed, two bedside lamps, a nightstand, a mirror, and a curtain.
A modern bathroom with a bathtub, a handheld showerhead, a towel rack, and a handheld shower control.

8. Sun Coast Inn

Sun Coast Inn
Englewood South
  • Shimmering blue waters beckon steps from pristine white sand beaches for ultimate holiday bliss.
AU$116
includes taxes & fees
3 Oct - 4 Oct
Sun Coast Inn
A pool area with a brick patio, lounge chairs, and a white fence.
A modern apartment with a living area, kitchen, and dining space.
A hotel room with two beds, a dark headboard, a large window with curtains, and a tiled floor.
A modern kitchen with grey cabinets, a black refrigerator, and a white countertop.

9. Englewood Inn & Suites

Englewood Inn & Suites
Englewood South
AU$109
includes taxes & fees
3 Oct - 4 Oct
Englewood Inn & Suites
A covered outdoor seating area with lounge chairs and tables, overlooking a beach with palm trees and a clear sky.
A thatched-roof outdoor seating area with tables and chairs, a grill, and a sign that reads "BBQ".
A living room with a sofa, a coffee table, and a patterned armchair. There is a dining area with a table and chairs.
A living room with a dark blue sofa, patterned armchair, white coffee table, and a view through glass doors to an outdoor patio.

10. Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
AU$451
includes taxes & fees
17 Oct - 18 Oct
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
View all properties

Choose what matters most at hotels with a pool in Gasparilla Island

Breakfast included
4 stars
5 stars
Spa pool
Spa

Top Gasparilla Island Hotel Reviews

Boca Grande Hotel

Boca Grande Hotel

10/10 Excellent
"Nancy “Jo” at the front desk is a true gem. The hotel is at the beginning of the island and is in a small plaza with everything you need. Kappys general store has golf cart rentals and all the basics for a great stay. The hotel was perfect. Off season is quiet with the pace picking up in October. South Beach restaurant is wonderful. The beach is superb. Great getaway for wife’s BD. Would return in a heartbeat."
Dennis 2-night trip
Posted 16 hours ago
Boca Grande Hotel
Sun Coast Inn

Sun Coast Inn

8/10 Good
"Good place near the beach but pool was not open or had water in it. Bummer ."
Michael 1-night trip
Posted 3 days ago
Sun Coast Inn

Explore a world of travel with Expedia