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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Gasparilla Island vacation homes

A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

1. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is AED 345
AED 1,335 total
includes taxes & fees
4 Nov - 5 Nov
Dreams Away - Sleeps 10 Pool Golf Fun
A modern kitchen with a central island, white cabinetry, and pendant lighting.

2. Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Oakland Hills
10.0 out of 10, Exceptional, (36 reviews)
"Everything we needed after a long day of fishing"
United States
WARREN R.
The price is AED 426
AED 1,278 total
includes taxes & fees
6 Nov - 7 Nov
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

3. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "
United States
Morgan P.
The price is AED 443
AED 1,456 total
includes taxes & fees
2 Nov - 3 Nov
Casa Florida 🌴 waterfront home with boat ramp
A beach with a clear sky, calm sea, and footprints on the sand.

4. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (6 reviews)
"The host was so nice I’ll be staying there again!"
United States
Melissa
The price is AED 290
AED 914 total
includes taxes & fees
7 Nov - 8 Nov
Charming 2-bedroom house in Englewood with WiFi and AC
A multi-level house with a white exterior, a staircase, and a deck area.

5. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
North Captiva Island
10.0 out of 10, Exceptional, (36 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

6. WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
10.0 out of 10, Exceptional, (29 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AED 393
AED 1,293 total
includes taxes & fees
1 Nov - 2 Nov
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
A modern kitchen with white cabinets, a marble island, pendant lighting, and a dining area with a sofa and table.

7. WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Oakland Hills
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AED 413
AED 1,223 total
includes taxes & fees
1 Nov - 2 Nov
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
A modern kitchen with white cabinets, a central island, pendant lighting, and a dining area with chairs and a table.

8. Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Oakland Hills
10.0 out of 10, Exceptional, (14 reviews)
"We will be booking again. it was perfect for us! very clean and everything you need to be comfortable."
United States
Kristen A.
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
A beach with footprints in the sand and a cloudy sky.

9. Nautical Nook

Nautical Nook
Englewood
9.8 out of 10, Exceptional, (16 reviews)
"It was super clean and the host was great"
United States
Dolores
The price is AED 384
AED 900 total
includes taxes & fees
1 Nov - 2 Nov
Nautical Nook
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink.

10. 2/2 Duplex on CANAL all updated; new furniture,

2/2 Duplex on CANAL all updated; new furniture,
Oakland Hills
9.6 out of 10, Exceptional, (10 reviews)
"awesome place"
United States
Brooke P.
The price is AED 404
AED 1,143 total
includes taxes & fees
16 Nov - 17 Nov
2/2 Duplex on CANAL all updated; new furniture,
A covered outdoor dining area with a table and chairs, large windows, and a ceiling fan.

11. Three Bedroom home with heated pool!

Three Bedroom home with heated pool!
Broadmoor
9.6 out of 10, Exceptional, (9 reviews)
"We had a wonderful stay"
United States
Julia H.
Three Bedroom home with heated pool!
An aerial view of a coastal area with several small islands connected by bridges.

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

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (52 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
The price is AED 918
AED 1,642 total
includes taxes & fees
1 Nov - 2 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

13. Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Oakland Hills
9.8 out of 10, Exceptional, (28 reviews)
"Great alternative to a hotel. Beautiful and clean."
United States
Sadie A.
The price is AED 588
AED 1,453 total
includes taxes & fees
10 Nov - 11 Nov
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
A modern kitchen with white cabinets, stainless steel appliances, a large island with bar stools, and a view of a green landscape through the glass door.

14. Golf & Beach Retreat Firepit BBQ Near Boca Grande

Golf & Beach Retreat Firepit BBQ Near Boca Grande
Oakland Hills
10.0 out of 10, Exceptional, (6 reviews)
"Great house and place to stay"
United States
Mike C.
The price is AED 496
AED 1,694 total
includes taxes & fees
1 Nov - 2 Nov
Golf & Beach Retreat Firepit BBQ Near Boca Grande
A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

15. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (11 reviews)
"Great property, very clean and host was extremely helpful. Great quiet neighborhood with friendly neighbors."
United States
Neal G.
The price is AED 537
AED 1,452 total
includes taxes & fees
1 Nov - 2 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A spacious living room with a flat-screen TV, a ceiling fan, and a large window offering a view of the outdoors.

16. HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.6 out of 10, Exceptional, (14 reviews)
"Clean, comfortable, has everything you need for a vacation"
United States
Rick J.
The price is AED 404
AED 1,743 total
includes taxes & fees
1 Nov - 2 Nov
HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
A swimming pool with a glass ceiling, a sofa, and a dining area.

17. Large house with heated walk-in pool near beaches!

Large house with heated walk-in pool near beaches!
Pinehurst
8.8 out of 10, Excellent, (25 reviews)
"Excellent place"
United States
Jeanne I.
Large house with heated walk-in pool near beaches!
A bedroom with a bed, a TV on a dresser, a clock on the wall, and a door leading to another room.

18. Tranquil and close to Englewood beach

Tranquil and close to Englewood beach
Englewood South
9.8 out of 10, Exceptional, (10 reviews)
"Clean and the Host was great! Will stay again!"
United States
Rob M.
The price is AED 360
AED 893 total
includes taxes & fees
9 Nov - 10 Nov
Tranquil and close to Englewood beach
A modern kitchen with a central island, stainless steel appliances, and three black bar stools.

19. Rotonda Retreat with Heated Pool, Golf, Beaches!

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (22 reviews)
"This was our second year staying here, and once again everything was absolutely perfect. The house was spotless, comfortable, and very well maintained. Check-in was smooth, communication was excellent, and everything was exactly as expected. We truly enjoyed our stay and felt right at home. We would happily come back again and highly recommend this place. Thank you for another wonderful stay!"
United States
Cesar C.
The price is AED 367
AED 1,604 total
includes taxes & fees
8 Nov - 9 Nov
Rotonda Retreat with Heated Pool, Golf, Beaches!
A spacious living room with a beige sofa, a glass coffee table, and a ceiling fan.

20. Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (74 reviews)
"Wonderful and comfortable stay close to the peace river! Jim was very responsive."
United States
Rebecca G.
The price is AED 298
AED 947 total
includes taxes & fees
1 Nov - 2 Nov
Completely remodeled beautiful waterfront property on canal with dock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gasparilla Island Hotel Reviews

The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

10/10 Excellent
"The room was fantastic, food was amazing and fairly priced. Already booked another trip"
Troy 7-night trip
Posted 2 days ago
The Suites at Fishermen’s Village

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