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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 $341
CA $771 total
includes taxes & fees
Nov 2 - Nov 3
Boat access only rental on private island

2. Selah Shores | Waterfront Getaway on Little Gasparilla Island

Selah Shores | Waterfront Getaway on Little Gasparilla Island
Placida
The price is CA $1,117
CA $1,349 total
includes taxes & fees
Nov 2 - Nov 3
Selah Shores | Waterfront Getaway on Little Gasparilla Island

3. 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 CA $127
CA $427 total
includes taxes & fees
Oct 3 - Oct 4
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

4. 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 CA $141
CA $441 total
includes taxes & fees
Oct 30 - Oct 31
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

5. 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 $127
CA $427 total
includes taxes & fees
Oct 4 - Oct 5
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

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, (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 CA $127
CA $427 total
includes taxes & fees
Oct 3 - Oct 4
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

7. 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.
The price is CA $100
CA $335 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom house in Englewood with WiFi and AC

8. 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 $127
CA $466 total
includes taxes & fees
Oct 15 - Oct 16
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

9. 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, (1,334 reviews)
"Excellent,clean y quiet"
United States
Carmen
The price is CA $249
CA $279 total
includes taxes & fees
Oct 30 - Oct 31
The Suites at Fishermen’s Village

10. 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)
"Everything we needed after a long day of fishing"
United States
WARREN R.
The price is CA $127
CA $474 total
includes taxes & fees
Oct 3 - Oct 4
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

11. 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 $126
CA $472 total
includes taxes & fees
Oct 3 - Oct 4
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

12. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 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 CA $214
CA $881 total
includes taxes & fees
Oct 6 - Oct 7
Chadwick Cove Resort & Marina

13. 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, (18 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is CA $125
CA $463 total
includes taxes & fees
Oct 15 - Oct 16
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

14. HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S
Oakland Hills
10.0 out of 10, Exceptional, (32 reviews)
"Beautiful home"
United States
Danail H.
The price is CA $121
CA $495 total
includes taxes & fees
Oct 18 - Oct 19
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

15. Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)

Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)
Manasota Key
10.0 out of 10, Exceptional, (2 reviews)
"This place has everything! Chris was friendly and helpful. I loved the location with a short walk to the beach and a view of the bay on the back porch. I will absolutely return"
United States
Christy S.
The price is CA $91
CA $416 total
includes taxes & fees
Oct 3 - Oct 4
Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)

16. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (19 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is CA $135
CA $482 total
includes taxes & fees
Oct 3 - Oct 4
Waterview Vacation Retreat Close To Ocean

17. Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
10.0 out of 10, Exceptional, (16 reviews)
"Very clean house, nice place to stay"
United States
Linda G.
The price is CA $111
CA $353 total
includes taxes & fees
Oct 16 - Oct 17
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

18. 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)
"This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. "
United States
Renay S.
The price is CA $240
CA $526 total
includes taxes & fees
Nov 2 - Nov 3
Turtle Cay at The Beach Shack! Come On Down!

19. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay and very spacious. Heather was a"
United States
Paul
The price is CA $149
CA $366 total
includes taxes & fees
Oct 3 - Oct 4
Nautical Nook

20. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is CA $152
CA $540 total
includes taxes & fees
Oct 3 - Oct 4
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
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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