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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
$500 nightly
The price is $553
Oct 7 - Oct 8
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
$844 nightly
The price is $938
Oct 9 - Oct 10
Total with taxes and fees
Selah Shores | Waterfront Getaway on Little Gasparilla Island
A beach with a thatched-roof structure, palm trees, and a view of the sea.

3. 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, (1,339 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 covered outdoor seating area with lounge chairs and tables, overlooking a beach with palm trees and a clear sky.

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
$270 nightly
The price is $299
Oct 7 - Oct 8
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.

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)
"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 7 - Oct 8
Total with taxes and fees
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
A large house with a thatched roof and multiple balconies, surrounded by lush tropical vegetation.

6. 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 11 - Oct 12
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.

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
$270 nightly
The price is $299
Oct 7 - Oct 8
Total with taxes and fees
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

8. 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
$560 nightly
The price is $604
Oct 11 - Oct 12
Total with taxes and fees
Chadwick Cove Resort & Marina
A modern kitchen with a central island, white cabinetry, and pendant lighting.

9. 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 7 - Oct 8
Total with taxes and fees
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
A beach with a clear sky, calm sea, and footprints on the sand.

10. 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.
$216 nightly
The price is $239
Oct 13 - Oct 14
Total with taxes and fees
Charming 2-bedroom house in Englewood with WiFi and AC
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, (19 reviews)
"Beautiful stay!"
United States
Terrica R.
$297 nightly
The price is $329
Oct 7 - Oct 8
Total with taxes and fees
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
A bedroom with a bed, two bedside tables, a ceiling fan, a window with curtains, a dresser, and a rug.

12. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
$387 nightly
The price is $434
Oct 12 - Oct 13
Total with taxes and fees
Dreams Away - Sleeps 10 Pool Golf Fun
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 7 - Oct 8
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
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
Oct 7 - Oct 8
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 stainless steel refrigerator, a microwave, and a sink.

15. 2/2 Duplex on CANAL all updated; new furniture,

2/2 Duplex on CANAL all updated; new furniture,
Oakland Hills
9.6 out of 10, Exceptional, (10 reviews)
"awesome place"
United States
Brooke P.
$294 nightly
The price is $325
Oct 16 - Oct 17
Total with taxes and fees
2/2 Duplex on CANAL all updated; new furniture,
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink. There are three bar stools and a dining table.

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.
$305 nightly
The price is $337
Oct 7 - Oct 8
Total with taxes and fees
Waterview Vacation Retreat Close To Ocean
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with seating.

17. 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)
"Beautiful home"
United States
Danail H.
$294 nightly
The price is $325
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 beach with footprints in the sand and a cloudy sky.

18. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (14 reviews)
"We loved our stay and it was perfect for our trip to explore the beaches and parks in the area. Clean spacious and had everything we needed. Very nice owners with extra touches of hospitality! Love this gem and will be back!"
United States
Tracie
$231 nightly
The price is $255
Oct 12 - Oct 13
Total with taxes and fees
Nautical Nook
A modern kitchen with a central island, stainless steel appliances, and three black bar stools.

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

Rotonda Retreat with Heated Pool, Golf, Beaches!
Oakland Hills
9.0 out of 10, Wonderful, (21 reviews)
"We really enjoyed this property!! "
United States
laura k.
$372 nightly
The price is $412
Oct 12 - Oct 13
Total with taxes and fees
Rotonda Retreat with Heated Pool, Golf, Beaches!
A modern kitchen with white cabinets, stainless steel appliances, a large island with bar stools, and a view of a green landscape through the glass door.

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.
$435 nightly
The price is $481
Oct 7 - Oct 8
Total with taxes and fees
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

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

8/10 Good
"CARING AND HELDFUL STAFF MEMBERS AND CLEAN ROOM"
MARLA June 2-night trip
Posted 3 hours ago
Baymont by Wyndham Punta Gorda/Port Charlotte

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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