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Little Gasparilla Island Vacation Rentals

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Our top choices for Little Gasparilla Island vacation rentals

1. 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 CA $266
CA $684 total
includes taxes & fees
Aug 18 - Aug 19
Boat access only rental on private island

2. 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 $729 total
includes taxes & fees
Aug 21 - Aug 22
Chadwick Cove Resort & Marina

3. 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 CA $144
CA $484 total
includes taxes & fees
Aug 18 - Aug 19
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

4. 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, (1,299 reviews)
"Great location and love the shops being under us. Great view and food options."
United States
Nathaniel
The price is CA $194
CA $218 total
includes taxes & fees
Aug 20 - Aug 21
The Suites at Fishermen’s Village- 2 Bedroom Suites

5. 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 $416 total
includes taxes & fees
Aug 18 - Aug 19
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

6. 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.
The price is CA $152
CA $495 total
includes taxes & fees
Aug 18 - Aug 19
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

7. 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 CA $124
CA $416 total
includes taxes & fees
Aug 18 - Aug 19
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

8. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (29 reviews)
"The property was very clean and conveniently located. "
United States
Chris F.
The price is CA $124
CA $491 total
includes taxes & fees
Aug 18 - Aug 19
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

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 CA $124
CA $416 total
includes taxes & fees
Aug 18 - Aug 19
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

10. 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 CA $147
CA $488 total
includes taxes & fees
Aug 18 - Aug 19
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

11. 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 $252
CA $530 total
includes taxes & fees
Aug 25 - Aug 26
MALU LANI Inn & Marina

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.
The price is CA $176
CA $525 total
includes taxes & fees
Aug 18 - Aug 19
Waterview Vacation Retreat Close To Ocean

13. 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.
The price is CA $193
CA $462 total
includes taxes & fees
Aug 18 - Aug 19
WALK TO BEACH ACCESS! DOG FRIENDLY! UNTI 1B

14. 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 $186
CA $335 total
includes taxes & fees
Aug 18 - Aug 19
Beautiful house with lake view

15. Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Oakland Hills
10.0 out of 10, Exceptional, (36 reviews)
"Very clean and served out brief visit well."
United States
Patricia M.
The price is CA $161
CA $505 total
includes taxes & fees
Aug 18 - Aug 19
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

16. Turtle Cay at The Beach Shack! Come On Down!

Turtle Cay at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (47 reviews)
"Yes everything was great had a wonderful time "
United States
Melinda M.
The price is CA $234
CA $516 total
includes taxes & fees
Aug 18 - Aug 19
Turtle Cay at The Beach Shack! Come On Down!

17. Large house with heated walk-in pool near beaches!

Large house with heated walk-in pool near beaches!
Pinehurst
8.6 out of 10, Excellent, (22 reviews)
"Excellent place"
United States
Jeanne I.
The price is CA $205
CA $690 total
includes taxes & fees
Aug 19 - Aug 20
Large house with heated walk-in pool near beaches!

18. HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful place to stay. Great location in close proximity to restaurants, shopping and the beach. Would certainly choose this home again."
United States
Brenda W.
The price is CA $180
CA $694 total
includes taxes & fees
Aug 18 - Aug 19
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-WASHER/DRYER-TENNIS-GOLF-BLISSFUL RETREAT

19. Modern Vacation House

Modern Vacation House
Pebble Beach
9.8 out of 10, Exceptional, (14 reviews)
"Everything went great. We enjoyed our stay."
United States
Mark A.
The price is CA $208
CA $520 total
includes taxes & fees
Aug 18 - Aug 19
Modern Vacation House

20. Waterfront Getaway, a Boating Paradise

Waterfront Getaway, a Boating Paradise
Englewood
10.0 out of 10, Exceptional, (61 reviews)
"Always an amazing stay"
United States
christine w.
The price is CA $206
CA $482 total
includes taxes & fees
Aug 18 - Aug 19
Waterfront Getaway, a Boating Paradise
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 Little Gasparilla Island Hotel Reviews

Find out more about Little 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 Little 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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