A shell on a beach with the sun setting in the background.

Little Gasparilla Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Little Gasparilla Island vacation rentals

A wooden staircase leading to a building with a sign reading 'Welcome to the Shore.'

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.
$457 nightly
The price is $506
Oct 17 - Oct 18
Total with taxes and fees
Boat access only rental on private island
A bedroom with a bed, a blue chair, a TV, and a balcony.

2. Selah Shores | Waterfront Getaway on Little Gasparilla Island

Selah Shores | Waterfront Getaway on Little Gasparilla Island
Placida
$849 nightly
The price is $943
Oct 19 - Oct 20
Total with taxes and fees
Selah Shores | Waterfront Getaway on Little Gasparilla Island
A covered outdoor seating area with lounge chairs and tables, overlooking a beach with palm trees and a clear sky.

3. 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)
"Beautiful property"
United States
Erin S.
$270 nightly
The price is $299
Oct 18 - Oct 19
Total with taxes and fees
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
A large house with a thatched roof and multiple balconies, surrounded by lush tropical vegetation.

4. 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.
$270 nightly
The price is $299
Oct 17 - Oct 18
Total with taxes and fees
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
A beachfront property with a covered patio, palm trees, and a wooden deck.

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, (51 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.
$270 nightly
The price is $299
Oct 17 - Oct 18
Total with taxes and fees
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
A beachfront property with a covered patio, palm trees, and a wooden deck.

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
$270 nightly
The price is $299
Oct 18 - Oct 19
Total with taxes and fees
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
A modern kitchen with a central island, white cabinetry, and pendant lighting.

7. 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.
$298 nightly
The price is $330
Oct 17 - Oct 18
Total with taxes and fees
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

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.
$297 nightly
The price is $329
Oct 17 - Oct 18
Total with taxes and fees
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
A beach with a thatched-roof structure, palm trees, and a view of the sea.

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, (1,346 reviews)
"Stay here every time I visit Florida. Highly recommend"
United States
Dawn
$175 nightly
The price is $196
Oct 30 - Oct 31
Total with taxes and fees
The Suites at Fishermen’s Village
A modern kitchen with white cabinets, a marble island, pendant lighting, and a dining area with a sofa and table.

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, (19 reviews)
"Beautiful stay!"
United States
Terrica R.
$297 nightly
The price is $329
Oct 17 - Oct 18
Total with taxes and fees
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

11. 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
$557 nightly
The price is $600
Oct 18 - Oct 19
Total with taxes and fees
Chadwick Cove Resort & Marina
A beach with a clear sky, calm sea, and footprints on the sand.

12. 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
$217 nightly
The price is $240
Oct 18 - Oct 19
Total with taxes and fees
Charming 2-bedroom house in Englewood with WiFi and AC
A beach at sunset with waves approaching the shore.

13. 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.
$298 nightly
The price is $330
Oct 17 - Oct 18
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
A covered outdoor dining area with a table and chairs, large windows, and a ceiling fan.

14. Three Bedroom home with heated pool!

Three Bedroom home with heated pool!
Broadmoor
9.6 out of 10, Exceptional, (9 reviews)
"We had a wonderful stay"
United States
Julia H.
$363 nightly
The price is $402
Oct 18 - Oct 19
Total with taxes and fees
Three Bedroom home with heated pool!
A modern kitchen with a central island, stainless steel appliances, and three black bar stools.

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

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (21 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.
$374 nightly
The price is $414
Oct 24 - Oct 25
Total with taxes and fees
Rotonda Retreat with Heated Pool, Golf, Beaches!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with seating.

16. 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, (33 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.
$301 nightly
The price is $332
Oct 18 - Oct 19
Total with taxes and fees
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink. There are three bar stools and a dining table.

17. 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.
$313 nightly
The price is $346
Oct 17 - Oct 18
Total with taxes and fees
Waterview Vacation Retreat Close To Ocean
A modern kitchen with white cabinets, a central island, pendant lighting, and a dining area with chairs and a table.

18. Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Oakland Hills
10.0 out of 10, Exceptional, (14 reviews)
"Very nice stay at a beautiful new home!!"
United States
Nancy H.
$319 nightly
The price is $352
Oct 17 - Oct 18
Total with taxes and fees
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

19. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
$325 nightly
The price is $364
Oct 18 - Oct 19
Total with taxes and fees
Dreams Away - Sleeps 10 Pool Golf Fun
An aerial view of a residential neighborhood with houses, lawns, and trees.

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, (33 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
$330 nightly
The price is $365
Oct 17 - Oct 18
Total with taxes and fees
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

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Nice room, great location and the rooftop bar and restaurant were very nice!"
Jeffrey 1-night trip
Posted 3 hours ago
Wyvern Hotel, an Ascend Collection Hotel

Find out more about Little Gasparilla Island

Everything you need to know about Little 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 Little 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 Little Gasparilla Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Little Gasparilla Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Little 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 $196 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 Little Gasparilla Island rentals

At Expedia, we put the best Little 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 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 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 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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