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
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Gasparilla Island historic hotels

A modern kitchen with white cabinetry, a dining area with a table and chairs, and a yellow accent wall.
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.

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

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
United States
Jennifer D.
AED 918
AED 1,723 total
includes taxes & fees
18 Oct - 19 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 modern kitchen with white cabinets, a dining area with two chairs, and a flat-screen TV mounted above the counter.
A covered patio area with a white chair, a table, and a bench.

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.
AED 545
AED 682 total
includes taxes & fees
18 Oct - 19 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 beach entrance with a rope barrier, a sign indicating private property, and a building with a thatched roof in the background.
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
AED 1,098
AED 2,344 total
includes taxes & fees
18 Oct - 19 Oct
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Beach
A pathway leading through a garden with various plants and trees.
A beach entrance with a rope barrier, a sign indicating private property, and a building with a thatched roof in the background.
A bedroom with a bed, a dresser, a TV, a ceiling fan, and a sliding glass door to a balcony.

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 traveler
AED 988
AED 2,303 total
includes taxes & fees
18 Oct - 19 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 two-story building with a balcony, surrounded by lush greenery and palm trees.
A modern hotel room with a bed, a sofa, a dining table, and a TV.
A beach pathway leading to beach chairs and thatched umbrellas, with a clear view of the ocean.

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.
AED 1,355
AED 2,681 total
includes taxes & fees
22 Oct - 23 Oct
Breathtaking Views - Romantic Honeymoon Suite - Jensen's "On the Gulf" 4
Beach
A white table with chairs on a wooden deck, overlooking lush greenery and palm trees.
A room with a large white door leading to an outdoor area with a wicker chair and a bottle of wine.
A pathway leading through a garden with various plants and trees.

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
AED 1,102
AED 2,454 total
includes taxes & fees
18 Oct - 19 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 two-story building with a balcony, surrounded by lush greenery and palm trees.
A covered outdoor dining area with a table set for two, surrounded by chairs, overlooking a view of the ocean and palm trees.
A pathway leading through a garden with various plants and 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.
AED 1,649
AED 3,165 total
includes taxes & fees
24 Oct - 25 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

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