A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

Gasparilla Island Vacation Rentals

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Our top choices for Gasparilla Island vacation rentals

1. Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Englewood
10.0 out of 10, Exceptional, (52 reviews)
"The stay was, as usual, very nice! I can’t say enough about how wonderful the management team is here!! Outstanding!! See you next year!!"
United States
Chris N.
The price is AED 327
AED 1,053 total
includes taxes & fees
14 Nov - 15 Nov
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

2. Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (54 reviews)
"It was a relaxing and beautiful stay!"
United States
Samantha I.
The price is AED 327
AED 1,053 total
includes taxes & fees
15 Nov - 16 Nov
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

3. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is AED 704
AED 1,443 total
includes taxes & fees
19 Nov - 20 Nov
MALU LANI Inn & Marina

4. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,371 reviews)
"Great place to stay but comes with a price."
United States
John
The price is AED 688
AED 770 total
includes taxes & fees
30 Nov - 1 Dec
The Suites at Fishermen’s Village

5. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (299 reviews)
"Such a cute place that we have never heard of! Walked to cute tiny shops, got awesome bbq……… very quaint and quiet. Had a great time."
United States
Shannon
The price is AED 486
AED 817 total
includes taxes & fees
15 Nov - 16 Nov
Matlacha Tiny Village

6. Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Englewood
10.0 out of 10, Exceptional, (64 reviews)
"The location was so convenient to the beaches. Very relaxing and a great place to go to truly feel like you are in a tropical oasis."
United States
Thomas
The price is AED 327
AED 1,017 total
includes taxes & fees
20 Nov - 21 Nov
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

7. Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (72 reviews)
"Beautiful property"
United States
Erin S.
The price is AED 327
AED 1,053 total
includes taxes & fees
15 Nov - 16 Nov
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

8. Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"peaceful and quiet in a great place to getaway"
United States
Louis
The price is AED 551
AED 878 total
includes taxes & fees
14 Nov - 15 Nov
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

9. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
North Captiva Island
9.8 out of 10, Exceptional, (38 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is AED 339
AED 3,490 total
includes taxes & fees
17 Nov - 18 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

10. Boat access only rental on private island

Boat access only rental on private island
Placida
10.0 out of 10, Exceptional, (13 reviews)
"We loved our stay, the house was as advertised! Great place to relax and enjoy the ocean!"
United States
Andrew S.
The price is AED 801
AED 2,065 total
includes taxes & fees
17 Nov - 18 Nov
Boat access only rental on private island

11. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (31 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is AED 531
AED 2,248 total
includes taxes & fees
17 Nov - 18 Nov
Chadwick Cove Resort & Marina

12. Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Oakland Hills
9.8 out of 10, Exceptional, (78 reviews)
"Great hosts and great stay! Would highly recommend."
United States
Kerry M.
The price is AED 393
AED 1,241 total
includes taxes & fees
14 Nov - 15 Nov
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

13. Turtle Cay at The Beach Shack! Come On Down!

Turtle Cay at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (47 reviews)
"I travel down South for business every so often and I'm always looking for a nice spot to stay. This place was great and extremely clean. Heather was great with responding to any questions I had. A lot of fun restaurants and local bars within less than a mile. I will be back."
United States
John M.
The price is AED 619
AED 1,351 total
includes taxes & fees
16 Nov - 17 Nov
Turtle Cay at The Beach Shack! Come On Down!

14. 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 426
AED 1,282 total
includes taxes & fees
14 Nov - 15 Nov
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

15. Nautical Nook

Nautical Nook
Englewood
9.8 out of 10, Exceptional, (16 reviews)
"It was super clean and the host was great"
United States
Dolores
Nautical Nook

16. 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 393
AED 1,241 total
includes taxes & fees
14 Nov - 15 Nov
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

17. 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, (6 reviews)
"The host was so nice I’ll be staying there again!"
United States
Melissa
The price is AED 353
AED 951 total
includes taxes & fees
23 Nov - 24 Nov
Charming 2-bedroom house in Englewood with WiFi and AC

18. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (30 reviews)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
The price is AED 184
AED 501 total
includes taxes & fees
14 Nov - 15 Nov
Charming cottage for 2 across warm mineral springs park

19. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (19 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is AED 446
AED 1,304 total
includes taxes & fees
14 Nov - 15 Nov
Waterview Vacation Retreat Close To Ocean

20. HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S
Oakland Hills
10.0 out of 10, Exceptional, (36 reviews)
"The cutest place to stay!! Owner was also very communicative. Perfect spot to get to everything fast. Will definitely stay here again"
United States
Alexis T.
The price is AED 347
AED 1,306 total
includes taxes & fees
15 Nov - 16 Nov
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S
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