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, (17 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is AED 370
AED 1,274 total
includes taxes & fees
9 Sep - 10 Sep
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Living area

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 417
AED 1,442 total
includes taxes & fees
22 Sep - 23 Sep
Casa Florida 🌴 waterfront home with boat ramp
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 184
AED 1,385 total
includes taxes & fees
9 Sep - 10 Sep
Rotonda Retreat with Heated Pool, Golf, Beaches!
Coffee/tea maker, fridge, microwave, oven

4. 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 1,160 total
includes taxes & fees
20 Sep - 21 Sep
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Dining

5. 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 468
AED 1,427 total
includes taxes & fees
17 Sep - 18 Sep
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
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)
"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
12 Sep - 13 Sep
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Coffee/tea maker, fridge, microwave, oven

7. 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
21 Sep - 22 Sep
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Interior

8. 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 1,304 total
includes taxes & fees
9 Sep - 10 Sep
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Sun loungers

9. 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 894 total
includes taxes & fees
10 Sep - 11 Sep
Charming 2-bedroom house in Englewood with WiFi and AC
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 1,349 total
includes taxes & fees
9 Sep - 10 Sep
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
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 1,191 total
includes taxes & fees
14 Sep - 15 Sep
2/2 Duplex on CANAL all updated; new furniture,
Interior

12. 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 331
AED 1,203 total
includes taxes & fees
9 Sep - 10 Sep
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Sun loungers, beach towels

13. 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
14 Sep - 15 Sep
NEW!! The “WATERSIDE” COTTAGE~With dockage
Pool

14. 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
10 Sep - 11 Sep
Three Bedroom home with heated pool!
Coffee/tea maker, fridge, microwave, oven

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 1,098 total
includes taxes & fees
12 Sep - 13 Sep
2-bedroom pool house with golf cart in Englewood, close to the beaches!
Coffee/tea maker, fridge, microwave, oven

16. 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 539
AED 1,805 total
includes taxes & fees
15 Sep - 16 Sep
Golf & Beach Retreat Firepit BBQ Near Boca Grande
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 951 total
includes taxes & fees
9 Sep - 10 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 1,834 total
includes taxes & fees
9 Sep - 10 Sep
Large house with heated walk-in pool near beaches!
Beach nearby, beach towels

19. 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
9 Sep - 10 Sep
Nautical Nook
Smart TV, stereo

20. Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (72 reviews)
"The house was very clean and perfect for our stay. The canal where we could keep the boat in the water was great, close to boat ramps too. There are things there you may would forget to bring, it was cool, well decorated and felt like a home. Jim was very responsive and helpful. 5 star all the way!We look forward to staying here again in the future."
United States
sherron c.
The price is AED 215
AED 843 total
includes taxes & fees
10 Sep - 11 Sep
Completely remodeled beautiful waterfront property on canal with dock
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

Holiday Inn Express & Suites Punta Gorda by IHG

Holiday Inn Express & Suites Punta Gorda by IHG

10/10 Excellent
"First off 5 stars to Stephanie at the front desk. Management take notice to this employee. The young lady never stopped, she worked the desk very well but was always moving. I saw her sweep, mop and was cleaning the window trim with a toothbrush. You just don't see that much anymore. The stay was great as is with most of the HIE that we have stayed at. staff was great everything clean. I do wish the pool was open a little longer than "dusk" and I think you should go back to the small containers of milk (nobody want to deal with that heavy glass pitcher) and bring back chocolate milk! Thanks!"
Steve 1-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Punta Gorda by IHG

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