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Gasparilla Island Holiday Rentals

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Our top choices for Gasparilla Island holiday 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 NZ$514
includes taxes & fees
15 Nov - 16 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 NZ$514
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 NZ$705
includes taxes & fees
23 Nov - 24 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 NZ$378
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, (300 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 NZ$372
includes taxes & fees
21 Nov - 22 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 NZ$512
includes taxes & fees
22 Nov - 23 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 NZ$512
includes taxes & fees
25 Nov - 26 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 NZ$424
includes taxes & fees
24 Nov - 25 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 NZ$1,705
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 NZ$1,014
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 NZ$1,104
includes taxes & fees
19 Nov - 20 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 NZ$608
includes taxes & fees
18 Nov - 19 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)
"This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. "
United States
Renay S.
The price is NZ$647
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 NZ$619
includes taxes & fees
27 Nov - 28 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
The price is NZ$440
includes taxes & fees
15 Nov - 16 Nov
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 NZ$599
includes taxes & fees
24 Nov - 25 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 NZ$462
includes taxes & fees
24 Nov - 25 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 NZ$246
includes taxes & fees
15 Nov - 16 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 NZ$630
includes taxes & fees
24 Nov - 25 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 NZ$624
includes taxes & fees
24 Nov - 25 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.

Find holiday rentals that suit your style

Find out more about Gasparilla Island

Everything you need to know about Gasparilla Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gasparilla Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gasparilla Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gasparilla Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gasparilla Island. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gasparilla Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gasparilla Island holiday rentals we have selected for you start as low as NZ$372 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gasparilla Island rentals

At Expedia, we put the best Gasparilla Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gasparilla Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gasparilla Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gasparilla Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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