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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 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 1,278 total
includes taxes & fees
7 Sep - 8 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 335
AED 1,151 total
includes taxes & fees
5 Sep - 6 Sep
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Coffee/tea maker, fridge, microwave, oven

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 403
AED 1,304 total
includes taxes & fees
5 Sep - 6 Sep
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Interior

4. 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 393
AED 1,289 total
includes taxes & fees
5 Sep - 6 Sep
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Coffee/tea maker, fridge, microwave, oven

5. 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 1,191 total
includes taxes & fees
6 Sep - 7 Sep
2/2 Duplex on CANAL all updated; new furniture,
Smart TV, foosball, table tennis

6. 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 367
AED 1,698 total
includes taxes & fees
7 Sep - 8 Sep
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Living area

7. 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 400
AED 1,412 total
includes taxes & fees
29 Sep - 30 Sep
Casa Florida 🌴 waterfront home with boat ramp
Interior

8. 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 1,211 total
includes taxes & fees
6 Sep - 7 Sep
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
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.
The price is AED 487
AED 1,451 total
includes taxes & fees
15 Sep - 16 Sep
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, (31 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is AED 360
AED 1,338 total
includes taxes & fees
6 Sep - 7 Sep
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Sun loungers

11. 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
9 Sep - 10 Sep
Charming 2-bedroom house in Englewood with WiFi and AC
Coffee/tea maker, fridge, microwave, oven

12. 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 1,527 total
includes taxes & fees
9 Sep - 10 Sep
Rotonda Retreat with Heated Pool, Golf, Beaches!
Pool

13. 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
6 Sep - 7 Sep
Three Bedroom home with heated pool!
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 991 total
includes taxes & fees
8 Sep - 9 Sep
2-bedroom pool house with golf cart in Englewood, close to the beaches!
Coffee/tea maker, fridge, microwave, oven

15. 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 522
AED 1,801 total
includes taxes & fees
8 Sep - 9 Sep
Golf & Beach Retreat Firepit BBQ Near Boca Grande
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 947 total
includes taxes & fees
5 Sep - 6 Sep
Snowbirds escape / vacation gateway
Indoor pool, a heated pool

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, (23 reviews)
"Excellent place"
United States
Jeanne I.
The price is AED 542
AED 1,819 total
includes taxes & fees
5 Sep - 6 Sep
Large house with heated walk-in pool near beaches!
Sun loungers, beach towels

18. 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
28 Sep - 29 Sep
NEW!! The “WATERSIDE” COTTAGE~With dockage
Beach nearby, beach towels

19. 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 937 total
includes taxes & fees
5 Sep - 6 Sep
Nautical Nook
Coffee/tea maker, fridge, microwave, oven

20. 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)
"We enjoyed the quaint little beach house. Not far from the beach. Plenty of places to go shopping and eating. Highly recommend it."
United States
kinz s.
The price is AED 258
AED 971 total
includes taxes & fees
7 Sep - 8 Sep
Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all
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

Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

8/10 Good
"Pleasant 5 day stay, close to beaches and commerce."
Christina 5-night trip
Posted less than an hour ago
Days Inn by Wyndham Port Charlotte/Punta Gorda

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