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

Little Gasparilla Island Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$496 nightly
The price is $549
Sep 23 - Sep 24
Total with taxes and fees
Boat access only rental on private island
A modern kitchen with white cabinetry, a central island with seating, and a built-in microwave.

2. Selah Shores | Waterfront Getaway on Little Gasparilla Island

Selah Shores | Waterfront Getaway on Little Gasparilla Island
Placida
$897 nightly
The price is $991
Sep 25 - Sep 26
Total with taxes and fees
Selah Shores | Waterfront Getaway on Little Gasparilla Island
A large house with a thatched roof and multiple balconies, surrounded by lush tropical vegetation.

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.
$270 nightly
The price is $299
Sep 23 - Sep 24
Total with taxes and fees
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
A beach at sunset with waves approaching the shore.

4. 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
Sep 23 - Sep 24
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
A beachfront property with a covered patio, palm trees, and a wooden deck.

5. 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
Sep 23 - Sep 24
Total with taxes and fees
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
A covered outdoor seating area with lounge chairs and tables, overlooking a beach with palm trees and a clear sky.

6. 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
$270 nightly
The price is $299
Sep 25 - Sep 26
Total with taxes and fees
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
A beachfront property with a covered patio, palm trees, and a wooden deck.

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)
"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
Sep 26 - Sep 27
Total with taxes and fees
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
A beach with a thatched-roof structure, palm trees, and a view of the sea.

8. 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, (1,326 reviews)
"Great place"
United States
Nidia
$160 nightly
The price is $179
Oct 4 - Oct 5
Total with taxes and fees
The Suites at Fishermen’s Village
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with seating.

9. 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, (31 reviews)
"Beautiful home"
United States
Danail H.
$301 nightly
The price is $332
Sep 23 - Sep 24
Total with taxes and fees
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

10. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.0 out of 10, Wonderful, (29 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
$564 nightly
The price is $608
Sep 23 - Sep 24
Total with taxes and fees
Chadwick Cove Resort & Marina
A modern kitchen with white cabinets, a marble island, pendant lighting, and a dining area with a sofa and table.

11. 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.
$297 nightly
The price is $329
Sep 23 - Sep 24
Total with taxes and fees
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink. There are three bar stools and a dining table.

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.
$305 nightly
The price is $337
Sep 23 - Sep 24
Total with taxes and fees
Waterview Vacation Retreat Close To Ocean
An aerial view of a residential neighborhood with houses, lawns, and trees.

13. 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
$309 nightly
The price is $343
Sep 23 - Sep 24
Total with taxes and fees
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

14. 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
Sep 23 - Sep 24
Total with taxes and fees
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
A modern kitchen with white cabinets, a central island, pendant lighting, and a dining area with chairs and a table.

15. 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.
$291 nightly
The price is $322
Sep 25 - Sep 26
Total with taxes and fees
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
A beach with a clear sky, calm sea, and footprints on the sand.

16. 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.
$220 nightly
The price is $243
Sep 23 - Sep 24
Total with taxes and fees
Charming 2-bedroom house in Englewood with WiFi and AC
A modern kitchen with a central island, white cabinetry, and pendant lighting.

17. 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
Sep 23 - Sep 24
Total with taxes and fees
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
A beach with clear water, a person walking, and a tree in the foreground.

18. 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.
$265 nightly
The price is $293
Sep 23 - Sep 24
Total with taxes and fees
Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

19. Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Oakland Hills
9.8 out of 10, Exceptional, (28 reviews)
"Great alternative to a hotel. Beautiful and clean."
United States
Sadie A.
$299 nightly
The price is $331
Sep 23 - Sep 24
Total with taxes and fees
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

20. Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"Property managers were very helpful to work with and will still stay again despite a hiccup. "
United States
Jennifer J.
$421 nightly
The price is $434
Sep 23 - Sep 24
Total with taxes and fees
Waterfront Condo Walkable to Everything with Beach Access
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

Four Points by Sheraton Punta Gorda Harborside

Four Points by Sheraton Punta Gorda Harborside

10/10 Excellent
"Awesome stay Bed was very comfortable. Room was fantastic. Tiki bar food was so so but it was a tiki bar. The atmosphere was really cool."
John 1-night trip
Posted 6 hours ago
Four Points by Sheraton Punta Gorda Harborside

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 $179 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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