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

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,327 reviews)
"Great place"
United States
Nidia
The price is £134
includes taxes & fees
4 Oct - 5 Oct
The Suites at Fishermen’s Village

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 £286
includes taxes & fees
1 Oct - 2 Oct
MALU LANI Inn & Marina

3. 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 £413
includes taxes & fees
27 Sept - 28 Sept
Boat access only rental on private island

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 £353
includes taxes & fees
27 Sept - 28 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage

5. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 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 £167
includes taxes & fees
29 Sept - 30 Sept
Matlacha Tiny Village

6. Relax under the Tiki Hut. Build memories! Without the Boca Grande price tag!!!

Relax under the Tiki Hut. Build memories! Without the Boca Grande price tag!!!
Englewood
10.0 out of 10, Exceptional, (17 reviews)
"This house was absolutely perfect for our large group to stay together! We had so much outdoor space to hangout together, but could still have our own space when needed. It was such a great stay!!"
United States
Karly L.
The price is £1,195
includes taxes & fees
25 Sept - 26 Sept
Relax under the Tiki Hut. Build memories! Without the Boca Grande price tag!!!

7. 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 £308
includes taxes & fees
7 Oct - 8 Oct
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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 £189
includes taxes & fees
27 Sept - 28 Sept
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

9. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.0 out of 10, Wonderful, (29 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 £464
includes taxes & fees
27 Sept - 28 Sept
Chadwick Cove Resort & Marina

10. 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, (70 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 £227
includes taxes & fees
25 Sept - 26 Sept
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

11. 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 £318
includes taxes & fees
6 Oct - 7 Oct
Casa Florida 🌴 waterfront home with boat ramp

12. 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 £227
includes taxes & fees
25 Sept - 26 Sept
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

13. 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 £230
includes taxes & fees
25 Sept - 26 Sept
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

14. 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 £371
includes taxes & fees
6 Oct - 7 Oct
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

15. 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, (97 reviews)
"Great place and will definitely stay here again."
United States
Jessica S.
The price is £358
includes taxes & fees
25 Sept - 26 Sept
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

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, (78 reviews)
"Nice stay in good location"
United States
John W.
The price is £250
includes taxes & fees
25 Sept - 26 Sept
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

17. 50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Matlacha
10.0 out of 10, Exceptional, (42 reviews)
"Excellent!"
United States
Tim A.
The price is £311
includes taxes & fees
25 Sept - 26 Sept
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

18. Beachfront Condo on Manasota Key

Beachfront Condo on Manasota Key
Manasota Key
9.6 out of 10, Exceptional, (135 reviews)
"Beautiful condo and amazing location will book again!"
United States
Charlie M.
The price is £637
includes taxes & fees
28 Sept - 29 Sept
Beachfront Condo on Manasota Key

19. 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)
"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 £230
includes taxes & fees
26 Sept - 27 Sept
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

20. Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!

Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!
Manasota Key
9.2 out of 10, Wonderful, (66 reviews)
"We had a great stay and will definitely stay here in the future"
United States
Brandon T.
The price is £347
includes taxes & fees
25 Sept - 26 Sept
Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!
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 £134 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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