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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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Gasparilla Island vacation rentals

Village Beach & Harbor Suite | Balcony view

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, (1,301 reviews)
"Great location and love the shops being under us. Great view and food options."
United States
Nathaniel
$179 nightly
The price is $201
Aug 25 - Aug 26
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites
Private beach nearby, motor boating, fishing

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
$331 nightly
The price is $360
Sep 9 - Sep 10
Total with taxes and fees
MALU LANI Inn & Marina
Exterior

3. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (295 reviews)
"We had a wonderful visit July 26th-28th. Check in was so easy. We stayed in the flamingo. The flamingo is so cute and charming. We had a wonderful time just relaxing and fishing off the dock with the grandkids. We love the kayaks. Tiny village is the perfect place for a little getaway and we can’t wait to book again."
United States
Heather
$185 nightly
The price is $198
Sep 9 - Sep 10
Total with taxes and fees
Matlacha Tiny Village
Pool

4. 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
$285 nightly
The price is $314
Aug 22 - Aug 23
Total with taxes and fees
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Sun loungers, beach towels

5. 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.
$339 nightly
The price is $373
Sep 1 - Sep 2
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage
Terrace/patio

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, (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
$273 nightly
The price is $302
Aug 22 - Aug 23
Total with taxes and fees
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
A heated pool

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.
$600 nightly
The price is $663
Aug 22 - Aug 23
Total with taxes and fees
3 bedroom 3 full bath beautiful house with heated pool and spa. 12 month minimum
Terrace/patio

8. 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.
$273 nightly
The price is $302
Aug 22 - Aug 23
Total with taxes and fees
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Dining

9. 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)
"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
$391 nightly
The price is $431
Aug 25 - Aug 26
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Coffee/tea maker, fridge, microwave, oven

10. 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.
$345 nightly
The price is $381
Aug 23 - Aug 24
Total with taxes and fees
Waterview Vacation Retreat Close To Ocean
Living area

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.
$331 nightly
The price is $366
Aug 25 - Aug 26
Total with taxes and fees
Casa Florida 🌴 waterfront home with boat ramp
Beach nearby, sun loungers, beach towels

12. WALK TO BEACH ACCESS! DOG FRIENDLY! UNTI 1B

WALK TO BEACH ACCESS! DOG FRIENDLY! UNTI 1B
Manasota Key
9.8 out of 10, Exceptional, (55 reviews)
"Great stay. Thought we would be closer the beach but stumpys service is great. Found the path and fished. Wonderful stay. Wish there was a tv in the master but nbd. "
United States
Amy B.
$313 nightly
The price is $346
Aug 22 - Aug 23
Total with taxes and fees
WALK TO BEACH ACCESS! DOG FRIENDLY! UNTI 1B
Dining

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.
$220 nightly
The price is $243
Aug 26 - Aug 27
Total with taxes and fees
Beautiful house with lake view
Exterior

14. 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
10.0 out of 10, Exceptional, (35 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
Beach nearby, sun loungers, beach towels

15. 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.
$319 nightly
The price is $352
Aug 22 - Aug 23
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Interior

16. 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.
$321 nightly
The price is $355
Aug 22 - Aug 23
Total with taxes and fees
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Exterior

17. 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.
$272 nightly
The price is $301
Aug 26 - Aug 27
Total with taxes and fees
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Coffee/tea maker, fridge, microwave, oven

18. 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.
$326 nightly
The price is $360
Aug 22 - Aug 23
Total with taxes and fees
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Exterior

19. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.2 out of 10, Wonderful, (26 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
$526 nightly
The price is $565
Aug 28 - Aug 29
Total with taxes and fees
Chadwick Cove Resort & Marina
Marina

20. 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, (41 reviews)
"I can't imagine a better place to stay and relax. They had everything you needed and more.I hope to come back in the future."
United States
George G.
$452 nightly
The price is $497
Aug 23 - Aug 24
Total with taxes and fees
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

10/10 Excellent
"Espectacular increíble es un 1000 de 10"
Melanie 2-night trip
Posted 12 hours ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Find out more about Gasparilla Island

Everything you need to know about Gasparilla Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gasparilla Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gasparilla Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Gasparilla Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $201 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gasparilla Island rentals

At Expedia, we put the best Gasparilla Island vacation 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 vacation.

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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