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Holiday Rentals in Little Gasparilla Island

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Our top choices for Little Gasparilla Island holiday 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 €511
includes taxes & fees
17 Nov - 18 Nov
Boat access only rental on private island

2. Selah Shores | A Waterfront Getaway on Little Gasparilla Island

Selah Shores | A Waterfront Getaway on Little Gasparilla Island
Placida
Selah Shores | A Waterfront Getaway on Little Gasparilla Island

3. 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 €264
includes taxes & fees
16 Nov - 17 Nov
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

4. 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, (52 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 €264
includes taxes & fees
16 Nov - 17 Nov
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

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, (72 reviews)
"Beautiful property"
United States
Erin S.
The price is €253
includes taxes & fees
24 Nov - 25 Nov
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

6. 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, (1,374 reviews)
"Great place to stay but comes with a price."
United States
John
The price is €190
includes taxes & fees
30 Nov - 1 Dec
The Suites at Fishermen’s Village

7. 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 €264
includes taxes & fees
19 Nov - 20 Nov
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

8. 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 €387
includes taxes & fees
16 Dec - 17 Dec
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

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)
"Great hosts and great stay! Would highly recommend."
United States
Kerry M.
The price is €307
includes taxes & fees
16 Nov - 17 Nov
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

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

11. 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, (6 reviews)
"The host was so nice I’ll be staying there again!"
United States
Melissa
Charming 2-bedroom house in Englewood with WiFi and AC

12. 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 €322
includes taxes & fees
16 Nov - 17 Nov
Waterview Vacation Retreat Close To Ocean

13. 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, (36 reviews)
"The cutest place to stay!! Owner was also very communicative. Perfect spot to get to everything fast. Will definitely stay here again"
United States
Alexis T.
The price is €323
includes taxes & fees
17 Nov - 18 Nov
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

14. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (31 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 €555
includes taxes & fees
17 Nov - 18 Nov
Chadwick Cove Resort & Marina

15. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is €319
includes taxes & fees
16 Nov - 17 Nov
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

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)
"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 €333
includes taxes & fees
1 Dec - 2 Dec
Turtle Cay at The Beach Shack! Come On Down!

17. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (300 reviews)
"Such a cute place that we have never heard of! Walked to cute tiny shops, got awesome bbq……… very quaint and quiet. Had a great time."
United States
Shannon
The price is €187
includes taxes & fees
21 Nov - 22 Nov
Matlacha Tiny Village

18. Rotonda Retreat with Heated Pool, Golf, Beaches!

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (23 reviews)
"This was our second year staying here, and once again everything was absolutely perfect. The house was spotless, comfortable, and very well maintained. Check-in was smooth, communication was excellent, and everything was exactly as expected. We truly enjoyed our stay and felt right at home. We would happily come back again and highly recommend this place. Thank you for another wonderful stay!"
United States
Cesar C.
Rotonda Retreat with Heated Pool, Golf, Beaches!

19. Nautical Nook

Nautical Nook
Englewood
9.8 out of 10, Exceptional, (16 reviews)
"It was super clean and the host was great"
United States
Dolores
The price is €226
includes taxes & fees
19 Nov - 20 Nov
Nautical Nook

20. Golf & Beach Retreat Firepit BBQ Near Boca Grande

Golf & Beach Retreat Firepit BBQ Near Boca Grande
Oakland Hills
10.0 out of 10, Exceptional, (6 reviews)
"Great house and place to stay"
United States
Mike C.
Golf & Beach Retreat Firepit BBQ Near Boca Grande
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

Everything you need to know about Little Gasparilla Island holiday rentals

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

Little Gasparilla Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Little Gasparilla Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Little Gasparilla Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Little Gasparilla Island holiday rentals we have selected for you start as low as €167 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Little Gasparilla Island rentals

At Expedia, we put the best Little Gasparilla Island holiday 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 Little 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 Little Gasparilla Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Little 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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