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- 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, (1,294 reviews)
"Really cute and calm beautiful place to stay."
United States
Maria
The price is CA $259
CA $290 total
includes taxes & fees
Aug 11 - Aug 12
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 CA $256
CA $535 total
includes taxes & fees
Aug 12 - Aug 13
MALU LANI Inn & Marina

3. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (294 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 CA $153
CA $276 total
includes taxes & fees
Aug 11 - Aug 12
Matlacha Tiny Village

4. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (27 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is CA $56
CA $185 total
includes taxes & fees
Aug 22 - Aug 23
Charming cottage for 2 across warm mineral springs park

5. 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 CA $124
CA $421 total
includes taxes & fees
Aug 11 - Aug 12
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

6. 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 CA $124
CA $421 total
includes taxes & fees
Aug 11 - Aug 12
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

7. 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 CA $124
CA $421 total
includes taxes & fees
Aug 11 - Aug 12
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

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 CA $209
CA $439 total
includes taxes & fees
Aug 11 - Aug 12
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

9. 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 CA $383
CA $924 total
includes taxes & fees
Aug 12 - Aug 13
3 bedroom 3 full bath beautiful house with heated pool and spa. 12 month minimum

10. 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 CA $238
CA $516 total
includes taxes & fees
Sep 8 - Sep 9
NEW!! The “WATERSIDE” COTTAGE~With dockage

11. 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 CA $232
CA $612 total
includes taxes & fees
Sep 8 - Sep 9
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

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, (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 CA $124
CA $418 total
includes taxes & fees
Aug 18 - Aug 19
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

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 CA $168
CA $313 total
includes taxes & fees
Aug 11 - Aug 12
Beautiful house with lake view

14. Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (9 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
The price is CA $91
CA $222 total
includes taxes & fees
Sep 1 - Sep 2
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

15. WALK TO BEACH ACCESS! DOG FRIENDLY PROPERTY! UNIT 2D

WALK TO BEACH ACCESS! DOG FRIENDLY PROPERTY! UNIT 2D
Manasota Key
9.6 out of 10, Exceptional, (43 reviews)
"Convenient location to the beach, very quiet location and perfect for the two of us. The welcome gifts were a special touch. Highly recommend staying here"
United States
Teresa S.
The price is CA $138
CA $373 total
includes taxes & fees
Aug 11 - Aug 12
WALK TO BEACH ACCESS! DOG FRIENDLY PROPERTY! UNIT 2D

16. Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is CA $120
CA $308 total
includes taxes & fees
Aug 11 - Aug 12
Nestled in North Port. Updated 2 Bed / 1 Bath.

17. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.2 out of 10, Wonderful, (25 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is CA $94
CA $733 total
includes taxes & fees
Aug 23 - Aug 24
Chadwick Cove Resort & Marina

18. 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 CA $144
CA $491 total
includes taxes & fees
Aug 11 - Aug 12
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

19. 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.
The price is CA $695
CA $1,845 total
includes taxes & fees
Aug 12 - Aug 13
Car-Free Island Escape | Pool, Spa + Golf Cart

20. Tiny home glamping unit in pine island on a 6 acre property

Tiny home glamping unit in pine island on a 6 acre property
Saint James City
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
The price is CA $195
CA $245 total
includes taxes & fees
Aug 11 - Aug 12
Tiny home glamping unit in pine island on a 6 acre property
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gasparilla Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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