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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Gasparilla Island vacation homes

A beach with a clear sky, calm sea, and footprints on the sand.

1. 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 257
AED 873 total
includes taxes & fees
1 Oct - 2 Oct
Charming 2-bedroom house in Englewood with WiFi and AC
A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

2. 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 387
AED 1,394 total
includes taxes & fees
1 Oct - 2 Oct
Casa Florida 🌴 waterfront home with boat ramp
A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

3. 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
1 Oct - 2 Oct
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.

4. 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 1,215 total
includes taxes & fees
2 Oct - 3 Oct
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.

5. 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)
"Very nice stay at a beautiful new home!!"
United States
Nancy H.
The price is AED 562
AED 1,446 total
includes taxes & fees
1 Oct - 2 Oct
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
A modern kitchen with a central island, white cabinetry, and pendant lighting.

6. 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)
The price is AED 327
AED 1,219 total
includes taxes & fees
1 Oct - 2 Oct
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
An outdoor patio with a table and chairs, a large umbrella, and a view of a lake and greenery.

7. Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.

Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.
Grove City
The price is AED 526
AED 1,510 total
includes taxes & fees
13 Oct - 14 Oct
Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.
A modern living room with a grey sofa, a white coffee table, and a ceiling fan.

8. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is AED 656
AED 1,720 total
includes taxes & fees
12 Oct - 13 Oct
Dreams Away - Sleeps 10 Pool Golf Fun
An aerial view of a residential neighborhood with houses, lawns, and trees.

9. 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 393
AED 1,389 total
includes taxes & fees
1 Oct - 2 Oct
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

10. 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 1,523 total
includes taxes & fees
1 Oct - 2 Oct
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.

11. 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 1,775 total
includes taxes & fees
1 Oct - 2 Oct
Golf & Beach Retreat Firepit BBQ Near Boca Grande
A spacious living room with a flat-screen TV, a ceiling fan, and a large window offering a view of the outdoors.

12. 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 367
AED 1,698 total
includes taxes & fees
6 Oct - 7 Oct
HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

13. 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.
The price is AED 578
AED 1,563 total
includes taxes & fees
3 Oct - 4 Oct
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink.

14. 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 1,194 total
includes taxes & fees
16 Oct - 17 Oct
2/2 Duplex on CANAL all updated; new furniture,
A modern kitchen with stainless steel appliances, a dining area with a marble countertop, and a living room with a sofa and TV.

15. 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
1 Oct - 2 Oct
2-bedroom pool house with golf cart in Englewood, close to the beaches!
An aerial view of a coastal area with several small islands connected by bridges.

16. 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 1,712 total
includes taxes & fees
1 Oct - 2 Oct
NEW!! The “WATERSIDE” COTTAGE~With dockage
A modern kitchen with white cabinets, stainless steel appliances, and a marble floor.

17. 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.
The price is AED 367
AED 1,146 total
includes taxes & fees
16 Oct - 17 Oct
Canal front new everything near Boca Grande Beach
A modern kitchen with a central island, stainless steel appliances, and three black bar stools.

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 1,512 total
includes taxes & fees
12 Oct - 13 Oct
Rotonda Retreat with Heated Pool, Golf, Beaches!
A covered outdoor dining area with a table and chairs, large windows, and a ceiling fan.

19. 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 1,761 total
includes taxes & fees
2 Oct - 3 Oct
Three Bedroom home with heated pool!
A swimming pool with a glass ceiling, a sofa, and a dining area.

20. 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, (24 reviews)
"Excellent place"
United States
Jeanne I.
The price is AED 542
AED 1,834 total
includes taxes & fees
1 Oct - 2 Oct
Large house with heated walk-in pool near beaches!
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
"Very nice place to stay"
James R 2-night trip
Posted 2 hours ago
The Suites at Fishermen’s Village

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