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

Gasparilla Island Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Gasparilla Island holiday rentals

A covered porch with wicker furniture, a glass table, and a view of the outdoors.

1. 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 HK$1,624
HK$4,141 total
includes taxes & fees
3 Nov - 4 Nov
Boat access only rental on private island
A covered outdoor seating area with lounge chairs and tables, overlooking a beach with palm trees and a clear sky.

2. 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, (71 reviews)
"Beautiful property"
United States
Erin S.
The price is HK$699
HK$2,250 total
includes taxes & fees
5 Nov - 6 Nov
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
A beachfront property with a covered patio, palm trees, and a wooden deck.

3. 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, (51 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 HK$699
HK$2,250 total
includes taxes & fees
3 Nov - 4 Nov
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
A waterfront patio with palm trees, a dock, and a boat.

4. 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 HK$1,518
HK$3,098 total
includes taxes & fees
3 Nov - 4 Nov
MALU LANI Inn & Marina
A large house with a thatched roof and multiple balconies, surrounded by lush tropical vegetation.

5. 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 HK$699
HK$2,250 total
includes taxes & fees
3 Nov - 4 Nov
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
A beachfront property with a covered patio, palm trees, and a wooden deck.

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 HK$777
HK$2,337 total
includes taxes & fees
19 Nov - 20 Nov
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
A covered outdoor deck with a table and chairs, overlooking a body of water and palm trees.

7. 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 HK$1,135
HK$4,801 total
includes taxes & fees
3 Nov - 4 Nov
Chadwick Cove Resort & Marina
A modern kitchen with a central island, stainless steel appliances, 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 HK$737
HK$2,852 total
includes taxes & fees
4 Nov - 5 Nov
Dreams Away - Sleeps 10 Pool Golf Fun
A beach with a thatched-roof structure, palm trees, and a view of the sea.

9. 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, (1,358 reviews)
"Amazing place to stay when visiting Punta Gorda. Very convenient and loved having shops and restaurants so close by. Spacious unit - so much better than just a hotel room."
United States
Michelle
The price is HK$1,632
HK$1,828 total
includes taxes & fees
3 Nov - 4 Nov
The Suites at Fishermen’s Village
A pool with a metal railing, surrounded by lush greenery and a covered area with a metal frame.

10. 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 HK$1,177
HK$1,875 total
includes taxes & fees
3 Nov - 4 Nov
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
A compact kitchen with a built-in seating area, a refrigerator, and a ceiling fan.

11. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (299 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is HK$1,003
HK$1,706 total
includes taxes & fees
3 Nov - 4 Nov
Matlacha Tiny Village
A modern living room with a sofa, a TV mounted on a wooden panel, and a kitchen area with a refrigerator, sink, and countertop.

12. 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 HK$628
HK$1,883 total
includes taxes & fees
7 Nov - 8 Nov
Charming 2-bedroom house in Englewood with WiFi and AC
A modern kitchen with a central island, white cabinetry, and pendant lighting.

13. 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 HK$911
HK$2,730 total
includes taxes & fees
6 Nov - 7 Nov
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
A covered outdoor dining area with a table and chairs, large windows, and a ceiling fan.

14. Three Bedroom home with heated pool!

Three Bedroom home with heated pool!
Broadmoor
9.6 out of 10, Exceptional, (9 reviews)
"We had a wonderful stay"
United States
Julia H.
Three Bedroom home with heated pool!
A modern kitchen with white cabinets, a marble island, pendant lighting, and a dining area with a sofa and table.

15. 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, (19 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is HK$883
HK$2,699 total
includes taxes & fees
3 Nov - 4 Nov
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

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 HK$840
HK$2,651 total
includes taxes & fees
6 Nov - 7 Nov
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
A dining area with a round wooden table, chairs, a coffee machine, a refrigerator, and a window with blinds.

17. 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
The price is HK$820
HK$1,922 total
includes taxes & fees
3 Nov - 4 Nov
Nautical Nook
A modern kitchen with white cabinets, a central island, pendant lighting, and a dining area with chairs and a table.

18. 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 will be booking again. it was perfect for us! very clean and everything you need to be comfortable."
United States
Kristen A.
The price is HK$1,200
HK$2,883 total
includes taxes & fees
8 Nov - 9 Nov
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
A multi-level house with a white exterior, a staircase, and a deck area.

19. 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
10.0 out of 10, Exceptional, (37 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is HK$725
HK$7,453 total
includes taxes & fees
3 Nov - 4 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
A residential area with houses, a beach, and a sunset.

20. 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 HK$1,322
HK$2,893 total
includes taxes & fees
3 Nov - 4 Nov
Turtle Cay at The Beach Shack! Come On Down!
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

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

10/10 Excellent
"The property is absolutely gorgeous…. The rooms are extremely comfortable and the amenities are perfect. So much fun!"
DeAnn 4-night trip
Posted 3 hours ago
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Find out more about Gasparilla Island

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