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

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Our top choices for Gasparilla Island holiday rentals

1. The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,292 reviews)
"Really cute and calm beautiful place to stay."
United States
Maria
The price is £154
includes taxes & fees
10 Aug - 11 Aug
The Suites at Fishermen’s Village- 2 Bedroom Suites

2. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is £285
includes taxes & fees
12 Aug - 13 Aug
MALU LANI Inn & Marina

3. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (293 reviews)
"Very nice alternative to a motel quite clean everything you need for your stay. highly recommend this property"
United States
PETER
The price is £147
includes taxes & fees
11 Aug - 12 Aug
Matlacha Tiny Village

4. 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 £297
includes taxes & fees
10 Aug - 11 Aug
NEW!! The “WATERSIDE” COTTAGE~With dockage

5. 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 £236
includes taxes & fees
10 Aug - 11 Aug
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

6. 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, (9 reviews)
"We had a wonderful stay. Beautiful home with a peaceful view. Great communication with the host. A nice quiet neighborhood. Would stay again. "
United States
Shauna
The price is £318
includes taxes & fees
10 Aug - 11 Aug
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

7. 3 bedroom 3 full bath beautiful house with heated pool and spa. 12 month minimum

3 bedroom 3 full bath beautiful house with heated pool and spa. 12 month minimum
South Gulf Cove
8.8 out of 10, Excellent, (9 reviews)
"We love the convenience in the amenities at the home and how close we were to the water and activities to do"
United States
kim o.
The price is £497
includes taxes & fees
11 Aug - 12 Aug
3 bedroom 3 full bath beautiful house with heated pool and spa. 12 month minimum

8. 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, (69 reviews)
"Excellent stay at Pura Vida——-clean, cool rooms, very relaxing experience on the property. It’s obvious Pura Vida put thought into the arrangement of outside amenities, including couches, dining tables, the spa, and numerous fruit trees planted around the property. Would 100% stay here again."
United States
Alex
The price is £225
includes taxes & fees
10 Aug - 11 Aug
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

9. 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, (62 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 £220
includes taxes & fees
18 Aug - 19 Aug
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

10. 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)
"Apartment was very clean! Lots of outdoor seating options. Nice beach chairs to take to the beach."
United States
Apryl H.
The price is £224
includes taxes & fees
10 Aug - 11 Aug
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

11. 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, (50 reviews)
"Very clean everything you need great location!"
United States
Laura B.
The price is £224
includes taxes & fees
10 Aug - 11 Aug
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

12. 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 £203
includes taxes & fees
6 Sept - 7 Sept
2-bedroom pool house with golf cart in Englewood, close to the beaches!

13. Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.6 out of 10, Exceptional, (16 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is £185
includes taxes & fees
11 Aug - 12 Aug
Beautiful house with lake view

14. Beach house - 3 min walk to beach!

Beach house - 3 min walk to beach!
Manasota Key
10.0 out of 10, Exceptional, (40 reviews)
"Fantastic location and a perfect space for a couple or a family. The property was spotless, and the beds and furniture were very comfortable. We really enjoyed our stay and would highly recommend it."
United States
Holly R.
The price is £335
includes taxes & fees
23 Aug - 24 Aug
Beach house - 3 min walk to beach!

15. Beachfront Condo on Manasota Key

Beachfront Condo on Manasota Key
Manasota Key
9.6 out of 10, Exceptional, (134 reviews)
"Beautiful condo and amazing location will book again!"
United States
Charlie M.
The price is £552
includes taxes & fees
10 Aug - 11 Aug
Beachfront Condo on Manasota Key

16. 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, (77 reviews)
"Nice stay in good location"
United States
John W.
The price is £254
includes taxes & fees
10 Aug - 11 Aug
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

17. 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 £257
includes taxes & fees
10 Aug - 11 Aug
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

18. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (18 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is £282
includes taxes & fees
16 Aug - 17 Aug
Waterview Vacation Retreat Close To Ocean

19. Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence
Matlacha
9.8 out of 10, Exceptional, (64 reviews)
"Great stay, would definitely go back! "
United States
Chad N.
The price is £799
includes taxes & fees
9 Sept - 10 Sept
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

20. 3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (94 reviews)
"Great place and will definitely stay here again."
United States
Jessica S.
The price is £348
includes taxes & fees
10 Aug - 11 Aug
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
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

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, apart-hotels, 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 £154 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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