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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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, (18 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AED 324
AED 1,175 total
includes taxes & fees
20 Sep - 21 Sep
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Coffee/tea maker, fridge, microwave, oven

2. 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 324
AED 1,215 total
includes taxes & fees
2 Oct - 3 Oct
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Interior

3. 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 327
AED 1,222 total
includes taxes & fees
2 Oct - 3 Oct
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Sun loungers

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, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is AED 275
AED 901 total
includes taxes & fees
20 Sep - 21 Sep
Charming 2-bedroom house in Englewood with WiFi and AC
Coffee/tea maker, fridge, microwave, oven

5. 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 588
AED 1,527 total
includes taxes & fees
2 Oct - 3 Oct
South West Family Home , 3 Bedroom 2 Bath, King bed suite, 4 Beds , 6 Guests
Aerial view

6. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is AED 360
AED 1,341 total
includes taxes & fees
20 Sep - 21 Sep
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Interior

7. 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 1,527 total
includes taxes & fees
2 Oct - 3 Oct
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Smart TV

8. Fabulous 3 BR & 3 BA canal house with heated pool near Boca Grande

Fabulous 3 BR & 3 BA canal house with heated pool near Boca Grande
Long Meadow
8.8 out of 10, Excellent, (3 reviews)
"Had a very nice stay just wish there were more tropical flowers planted around the property the flower beds were all weeds and grass needed cutting, the pool got cleaned the day before we left so really had no pool time."
United States
Gloria R.
The price is AED 397
AED 1,818 total
includes taxes & fees
20 Sep - 21 Sep
Fabulous 3 BR & 3 BA canal house with heated pool near Boca Grande
Pool

9. 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.
Three Bedroom home with heated pool!
Coffee/tea maker, fridge, microwave, oven

10. 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 459
AED 1,101 total
includes taxes & fees
20 Sep - 21 Sep
2-bedroom pool house with golf cart in Englewood, close to the beaches!
Dining

11. 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)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Living area

12. 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 395
AED 1,348 total
includes taxes & fees
5 Oct - 6 Oct
Casa Florida 🌴 waterfront home with boat ramp
Coffee/tea maker, fridge, microwave, oven

13. 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.
2/2 Duplex on CANAL all updated; new furniture,
Private kitchen

14. Canal front new everything near Boca Grande Beach

Canal front new everything near Boca Grande Beach
Oakland Hills
8.4 out of 10, Very good, (6 reviews)
"We stayed for one month. Property was very clean, outside finishing up on storm repairs and completed couple days after we arrived. Safe area away from noise, but close drive to beaches and restaurants."
United States
Kristine G.
Canal front new everything near Boca Grande Beach
Sun loungers, beach towels

15. 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 918
AED 1,723 total
includes taxes & fees
21 Sep - 22 Sep
NEW!! The “WATERSIDE” COTTAGE~With dockage
Indoor pool, a heated pool

16. 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, (23 reviews)
"Excellent place"
United States
Jeanne I.
The price is AED 542
AED 1,823 total
includes taxes & fees
20 Sep - 21 Sep
Large house with heated walk-in pool near beaches!
Beach nearby, beach towels

17. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay and very spacious. Heather was a"
United States
Paul
The price is AED 384
AED 937 total
includes taxes & fees
20 Sep - 21 Sep
Nautical Nook
Coffee/tea maker, fridge, microwave, oven

18. 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 294
AED 1,468 total
includes taxes & fees
12 Oct - 13 Oct
Rotonda Retreat with Heated Pool, Golf, Beaches!
Coffee/tea maker, fridge, microwave, oven

19. 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 509
AED 1,793 total
includes taxes & fees
21 Sep - 22 Sep
Golf & Beach Retreat Firepit BBQ Near Boca Grande
Coffee/tea maker, fridge, microwave, oven

20. 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 955 total
includes taxes & fees
20 Sep - 21 Sep
Snowbirds escape / vacation gateway
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
"Great place ! Love the rooftop pool ! Nice clean rooms , good size. Helpful staff. Could use more Choices and better hours for the food court."
Wayne 4-night trip
Posted 7 hours ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

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