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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Our top choices for Gasparilla Island vacation 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, (1,306 reviews)
"Great place"
United States
Nidia
$176 nightly
The price is $197
Sep 3 - Sep 4
Total with taxes and fees
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
$340 nightly
The price is $370
Sep 3 - Sep 4
Total with taxes and fees
MALU LANI Inn & Marina

3. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (296 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
$207 nightly
The price is $223
Sep 10 - Sep 11
Total with taxes and fees
Matlacha Tiny Village

4. 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.
$503 nightly
The price is $556
Aug 31 - Sep 1
Total with taxes and fees
Boat access only rental on private island

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
$286 nightly
The price is $315
Aug 31 - Sep 1
Total with taxes and fees
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, (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
$360 nightly
The price is $396
Sep 9 - Sep 10
Total with taxes and fees
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

7. 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.
$337 nightly
The price is $371
Sep 2 - Sep 3
Total with taxes and fees
NEW!! The “WATERSIDE” COTTAGE~With dockage

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 31 - Sep 1
Total with taxes and fees
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

9. 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.
$305 nightly
The price is $337
Aug 31 - Sep 1
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

10. 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, (63 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 31 - Sep 1
Total with taxes and fees
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

11. 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)
"Pet friendly and close to beaches. Clean place and quiet area"
United States
Marta D.
$313 nightly
The price is $346
Aug 31 - Sep 1
Total with taxes and fees
WALK TO BEACH ACCESS! DOG FRIENDLY! UNTI 1B

12. 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.
$332 nightly
The price is $367
Aug 31 - Sep 1
Total with taxes and fees
Waterview Vacation Retreat Close To Ocean

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.
$273 nightly
The price is $302
Aug 31 - Sep 1
Total with taxes and fees
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

14. 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
$272 nightly
The price is $301
Sep 26 - Sep 27
Total with taxes and fees
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

15. Car-Free Island Escape | Pool, Spa + Golf Cart

Car-Free Island Escape | Pool, Spa + Golf Cart
North Captiva
10.0 out of 10, Exceptional, (12 reviews)
"We had an excellent stay. "
United States
Ana A.
$1,107 nightly
The price is $1,219
Sep 2 - Sep 3
Total with taxes and fees
Car-Free Island Escape | Pool, Spa + Golf Cart

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.
$316 nightly
The price is $349
Aug 31 - Sep 1
Total with taxes and fees
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

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, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
$213 nightly
The price is $235
Aug 31 - Sep 1
Total with taxes and fees
Charming 2-bedroom house in Englewood with WiFi and AC

18. 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, (95 reviews)
"Great place and will definitely stay here again."
United States
Jessica S.
$404 nightly
The price is $446
Aug 31 - Sep 1
Total with taxes and fees
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

19. 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.
$322 nightly
The price is $356
Aug 31 - Sep 1
Total with taxes and fees
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

20. Ultra Modern Home w Heated Salt water Pool pet friendly

Ultra Modern Home w Heated Salt water Pool pet friendly
Mariner
10.0 out of 10, Exceptional, (19 reviews)
"Host very responsive to questions! Really enjoyed the pool and on site amenities!"
United States
Doug M.
$413 nightly
The price is $455
Aug 31 - Sep 1
Total with taxes and fees
Ultra Modern Home w Heated Salt water Pool pet friendly
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 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 $197 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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