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
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 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 1,208 total
includes taxes & fees
14 Sep - 15 Sep
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Coffee/tea maker, fridge, microwave, oven

2. 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 had a wonderful month long stay. This home is nicely and tastefully decorated, clean and welcoming. Our host was very attentive to our needs and provided quick communication. Lots of extras for our trips to the beach. We would definitely stay here again!"
United States
Amber G.
The price is AED 353
AED 1,174 total
includes taxes & fees
20 Sep - 21 Sep
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Sun loungers

3. 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
14 Sep - 15 Sep
Charming 2-bedroom house in Englewood with WiFi and AC
Smart TV, foosball, table tennis

4. 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)
"Clean, comfortable, has everything you need for a vacation"
United States
Rick J.
The price is AED 367
AED 1,695 total
includes taxes & fees
14 Sep - 15 Sep
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Coffee/tea maker, fridge, microwave, oven

5. 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 1,208 total
includes taxes & fees
14 Sep - 15 Sep
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Living area

6. 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 520
AED 1,572 total
includes taxes & fees
14 Oct - 15 Oct
Casa Florida 🌴 waterfront home with boat ramp
Interior

7. 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 1,211 total
includes taxes & fees
14 Sep - 15 Sep
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Coffee/tea maker, fridge, microwave, oven

8. 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
14 Sep - 15 Sep
2/2 Duplex on CANAL all updated; new furniture,
Dining

9. 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
Aerial view

10. 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 1,382 total
includes taxes & fees
14 Sep - 15 Sep
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Sun loungers, beach towels

11. 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
16 Sep - 17 Sep
NEW!! The “WATERSIDE” COTTAGE~With dockage
Coffee/tea maker, fridge, microwave, oven

12. 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 536
AED 1,783 total
includes taxes & fees
26 Sep - 27 Sep
Golf & Beach Retreat Firepit BBQ Near Boca Grande
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 1,208 total
includes taxes & fees
15 Sep - 16 Sep
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Beach nearby, beach towels

14. 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
14 Sep - 15 Sep
Nautical Nook
Pool

15. 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 1,728 total
includes taxes & fees
14 Sep - 15 Sep
Three Bedroom home with heated pool!
Coffee/tea maker, fridge, microwave, oven

16. 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
18 Sep - 19 Sep
2-bedroom pool house with golf cart in Englewood, close to the beaches!
Coffee/tea maker, fridge, microwave, oven

17. 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
14 Sep - 15 Sep
Snowbirds escape / vacation gateway
Indoor pool, a heated pool

18. 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 1,779 total
includes taxes & fees
14 Sep - 15 Sep
Large house with heated walk-in pool near beaches!
Coffee/tea maker, fridge, microwave, oven

19. Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all

Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all
Englewood Central
10.0 out of 10, Exceptional, (4 reviews)
"This was a beautiful home with everything close by, shops and beach. It has a large outdoor screened in porch, perfect for chilling with the kids!"
United States
Loren J.
The price is AED 258
AED 964 total
includes taxes & fees
26 Sep - 27 Sep
Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all
Smart TV

20. Spacious 4BR Escape with Heated Saltwater Pool & Hot Tub – Near Beaches & Golf

Spacious 4BR Escape with Heated Saltwater Pool & Hot Tub – Near Beaches & Golf
Long Meadow
10.0 out of 10, Exceptional, (7 reviews)
"The house was just what we wanted. "
United States
Keith L.
The price is AED 694
AED 2,386 total
includes taxes & fees
14 Sep - 15 Sep
Spacious 4BR Escape with Heated Saltwater Pool & Hot Tub – Near Beaches & Golf
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

Hampton Inn & Suites North Port

Hampton Inn & Suites North Port

10/10 Excellent
"We have stayed at this location many times. The staff is always friendly. The rooms are well maintained and very comfortable. The breakfast offers a nice assortment."
Edward 3-night trip
Posted 13 hours ago
Hampton Inn & Suites North Port

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