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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Gasparilla Island vacation homes

Interior

1. 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, (17 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AED 370
AED 1,282 total
includes taxes & fees
31 Aug - 1 Sep
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Sun loungers

2. 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, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is AED 275
AED 898 total
includes taxes & fees
31 Aug - 1 Sep
Charming 2-bedroom house in Englewood with WiFi and AC
Coffee/tea maker, fridge, microwave, oven

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

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (21 reviews)
"We really enjoyed this property!! "
United States
laura k.
The price is AED 220
AED 1,441 total
includes taxes & fees
31 Aug - 1 Sep
Rotonda Retreat with Heated Pool, Golf, Beaches!
Living area

4. 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 434
AED 1,468 total
includes taxes & fees
29 Sep - 30 Sep
Casa Florida 🌴 waterfront home with boat ramp
Sun loungers, beach towels

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

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (51 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 698
AED 1,455 total
includes taxes & fees
1 Sep - 2 Sep
NEW!! The “WATERSIDE” COTTAGE~With dockage
Dining

6. 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, (10 reviews)
"We had a wonderful stay. Beautiful home with a peaceful view. Great communication with the host. A nice quiet neighborhood. Would stay again. "
United States
Shauna
The price is AED 509
AED 1,494 total
includes taxes & fees
13 Sep - 14 Sep
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Aerial view

7. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is AED 327
AED 1,315 total
includes taxes & fees
31 Aug - 1 Sep
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Coffee/tea maker, fridge, microwave, oven

8. 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 403
AED 1,308 total
includes taxes & fees
9 Sep - 10 Sep
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Interior

9. 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)
"Very clean and served out brief visit well."
United States
Patricia M.
The price is AED 393
AED 1,311 total
includes taxes & fees
2 Sep - 3 Sep
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Indoor pool, a heated pool

10. HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful place to stay. Great location in close proximity to restaurants, shopping and the beach. Would certainly choose this home again."
United States
Brenda W.
The price is AED 331
AED 1,672 total
includes taxes & fees
31 Aug - 1 Sep
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Coffee/tea maker, fridge, microwave, oven

11. 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)
"Great place, nice area. House was clean and furnished as expected. Only problem was there was an ant infestation so we had to keep everything off the floor."
United States
Steve C.
The price is AED 404
AED 1,205 total
includes taxes & fees
31 Aug - 1 Sep
2/2 Duplex on CANAL all updated; new furniture,
Coffee/tea maker, fridge, microwave, oven

12. South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests

South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests
Oakland Hills
9.6 out of 10, Exceptional, (5 reviews)
"This was the perfect location for our stay. It was clean, comfortable, and well equipped."
United States
Dorian D.
The price is AED 349
AED 1,230 total
includes taxes & fees
1 Sep - 2 Sep
South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests
Interior

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 349
AED 1,230 total
includes taxes & fees
1 Sep - 2 Sep
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Coffee/tea maker, fridge, microwave, oven

14. 2-bedroom pool house with golf cart in Englewood, close to the beaches!

2-bedroom pool house with golf cart in Englewood, close to the beaches!
Grove City
10.0 out of 10, Exceptional, (10 reviews)
"Great stay, great host, and a great time!"
United States
Christopher G.
The price is AED 367
AED 998 total
includes taxes & fees
8 Sep - 9 Sep
2-bedroom pool house with golf cart in Englewood, close to the beaches!
Outdoor dining

15. Luxe 3BR Waterfront Stay in Cape Coral

Luxe 3BR Waterfront Stay in Cape Coral
Mariner
10.0 out of 10, Exceptional, (12 reviews)
"We were pleased with our stay. "
United States
Jamie G.
The price is AED 230
AED 1,094 total
includes taxes & fees
31 Aug - 1 Sep
Luxe 3BR Waterfront Stay in Cape Coral
Coffee/tea maker, fridge, microwave, oven

16. Snowbirds escape / vacation gateway

Snowbirds escape / vacation gateway
Englewood East
8.8 out of 10, Excellent, (15 reviews)
"Host was very fast to respond, understanding, and accommodating. Pool is offsite but we spent our time at the beach. Overall satisfied and would stay again."
United States
Logan C.
The price is AED 393
AED 959 total
includes taxes & fees
3 Sep - 4 Sep
Snowbirds escape / vacation gateway
Pool

17. Three Bedroom home with heated pool!

Three Bedroom home with heated pool!
Broadmoor
9.6 out of 10, Exceptional, (9 reviews)
"The house was very nice, clean, and comfortable. Communication with the owner/host was generally excellent"
United States
Annette A.
The price is AED 484
AED 1,746 total
includes taxes & fees
1 Sep - 2 Sep
Three Bedroom home with heated pool!
Coffee/tea maker, fridge, microwave, oven

18. 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 529
AED 1,827 total
includes taxes & fees
31 Aug - 1 Sep
Golf & Beach Retreat Firepit BBQ Near Boca Grande
TV, fireplace

19. Chic 3BR, 2BA – Brand New!

Chic 3BR, 2BA – Brand New!
Englewood East
The price is AED 272
AED 1,230 total
includes taxes & fees
31 Aug - 1 Sep
Chic 3BR, 2BA – Brand New!
Beach nearby, beach towels

20. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (10 reviews)
"Great place to stay and very spacious. Heather was a"
United States
Paul
The price is AED 384
AED 951 total
includes taxes & fees
31 Aug - 1 Sep
Nautical Nook
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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

10/10 Excellent
"Best Resort ever."
Yunior 2-night trip
Posted 2 hours ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

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