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

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Check availability on Gasparilla Island Historic Hotels

Tonight
3 Oct - 4 Oct
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4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Gasparilla Island historic hotels

An aerial view of a coastal area with several small islands connected by bridges.
A nighttime view of a paved pathway flanked by palm trees and a building with illuminated windows.
A modern kitchen with a central island, white chairs, and a yellow accent wall.
A modern living room with a beige sectional sofa, a round armchair, a glass coffee table, and a striped rug.

1. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
United States
Jennifer D.
£362
includes taxes & fees
4 Oct - 5 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage
A bedroom with a bed, a desk, and a chair. There is a kitchen area with a refrigerator, sink, and cabinets.
Angler's Inn with a colorful facade, a parking area, and palm trees in the background.
A compact kitchen with white cabinets, a stainless steel refrigerator, a sink, and a window with blinds.
A modern kitchen with white cabinets, a dining area with two chairs, and a flat-screen TV mounted above the counter.

2. Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Matlacha
United States
Nicolette K.
£143
includes taxes & fees
4 Oct - 5 Oct
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
A beach pathway leading to beach chairs and thatched umbrellas, with a clear view of the ocean.
A beachside room with a table and chairs, a bottle of wine, and a view of the beach and ocean.
A garden with palm trees, a gravel path, and a post office sign.
A bedroom with a bed, a ceiling fan, a nightstand, and a dresser.

3. Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1

Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Captiva
United States
Bryant
£489
includes taxes & fees
5 Oct - 6 Oct
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Beach
A beach entrance with a rope barrier, a sign indicating private property, and a building with a thatched roof in the background.
A covered outdoor seating area with a table and chairs, surrounded by lush greenery.
A pathway leading through a garden with various plants and trees.

4. Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7

Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7
Captiva
United States
Anonymous traveller
£480
includes taxes & fees
4 Oct - 5 Oct
Historic Captiva PO Cottage Garden Suite Steps to Beach Casual Lux Décor - Jensen's "On the Gulf" 7
A covered outdoor seating area with a table and chairs, overlooking a beach.
A beach pathway leading to beach chairs and thatched umbrellas, with a clear view of the ocean.
A pathway leading through a garden with various plants and trees.
A modern hotel room with a bed, a sofa, a dining table, and a TV.

5. Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4

Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4
Captiva
United States
Christy F.
£568
includes taxes & fees
4 Oct - 5 Oct
Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4
Beach
A pathway leading through a garden with various plants and trees.
A modern building with a glass facade, surrounded by tropical vegetation and outdoor seating.
A room with a large white door leading to an outdoor area with a wicker chair and a bottle of wine.

6. Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6

Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6
Captiva
United States
Juan
£511
includes taxes & fees
4 Oct - 5 Oct
Historic PO Cottage Garden Suite Steps to Beach - Casual Lux Décor - Jensen's "On the Gulf" 6
A coastal residential area with beachfront properties, a sandy beach, and ocean views.
A modern living room with a grey sofa, ottoman, and a coffee table. There is a kitchen area in the background with white cabinets and a microwave.
A pathway leading through a garden with various plants and trees.
A covered outdoor dining area with a table set for two, surrounded by chairs, overlooking a view of the ocean and palm trees.

7. Best Views & Beach on Captiva - Jensen's “On the Gulf” - Casual Lux - South Beach Suite 3

Best Views & Beach on Captiva - Jensen's “On the Gulf” - Casual Lux - South Beach Suite 3
Captiva
United States
john E.
£650
includes taxes & fees
4 Oct - 5 Oct
Best Views & Beach on Captiva - Jensen's “On the Gulf” - Casual Lux - South Beach Suite 3
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Top Gasparilla Island Hotel Reviews

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

8/10 Good
"Upon arrival there was no one around to check in. It was because they were helping another guest who needed help. After dinner I came back and check in was smooth and everything was great."
Brian 1-night trip
Posted 1 day ago
Baymont by Wyndham Punta Gorda/Port Charlotte

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