A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

Search Villas in Gasparilla Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Gasparilla Island villas

A bright green house with a white picket fence, a wooden staircase, and a picnic table.

1. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (298 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is AED 486
AED 817 total
includes taxes & fees
31 Oct - 1 Nov
Matlacha Tiny Village
A residential area with houses, a beach, and a sunset.

2. 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 AED 619
AED 1,355 total
includes taxes & fees
1 Nov - 2 Nov
Turtle Cay at The Beach Shack! Come On Down!
An outdoor patio area with a seating arrangement, a hammock, and a view of a grassy yard and trees.

3. 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 AED 393
AED 1,293 total
includes taxes & fees
1 Nov - 2 Nov
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
A modern two-story house with a brick driveway and a well-maintained lawn.

4. 3BR Boundary Breeze Heated Pool Beach Golf Nearby

3BR Boundary Breeze Heated Pool Beach Golf Nearby
Oakland Hills
10.0 out of 10, Exceptional, (3 reviews)
"Clean. Fast communication. Lots of space for our stay. Will stay again next time we drive down for the weekend!"
United States
Catherine P.
3BR Boundary Breeze Heated Pool Beach Golf Nearby
A two-story house with a well-maintained lawn and palm trees.

5. Stunning Villa in Golfer's Paradise/Canal Views

Stunning Villa in Golfer's Paradise/Canal Views
Long Meadow
9.6 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay. Beautiful house with plenty of space. Enjoyed lanai with great sunsets. Would stay again."
United States
Carol C.
The price is AED 590
AED 1,998 total
includes taxes & fees
31 Oct - 1 Nov
Stunning Villa in Golfer's Paradise/Canal Views
A residential area with houses, a marina, and a body of water.

6. Seashell Shanty at The Beach Shack! Come On Down!

Seashell Shanty at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place and a great location "
United States
Matthew C.
The price is AED 619
AED 1,355 total
includes taxes & fees
1 Nov - 2 Nov
Seashell Shanty at The Beach Shack! Come On Down!
A single-story house with a flat roof, large windows, and a small porch area.

7. "Sea Dunes" 3 bedrooms 2 bath

"Sea Dunes" 3 bedrooms 2 bath
Port Charlotte
7.4 out of 10, Good, (3 reviews)
"For our purposes, shopping and other activities were close enough. "
United States
Charles H.
The price is AED 257
AED 1,439 total
includes taxes & fees
31 Oct - 1 Nov
"Sea Dunes" 3 bedrooms 2 bath
A residential area with a pond, palm trees, and houses with sloped roofs.

8. 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 AED 463
AED 1,393 total
includes taxes & fees
1 Nov - 2 Nov
Waterview Vacation Retreat Close To Ocean
A turquoise building with a tiled driveway and a row of bicycles parked in front.

9. Flamingo's Nest at the Beach Shack. Just one block from the beach!

Flamingo's Nest at the Beach Shack. Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (44 reviews)
"Location was great, property condition is excellent!"
United States
Mabel
The price is AED 619
AED 1,322 total
includes taxes & fees
1 Nov - 2 Nov
Flamingo's Nest at the Beach Shack. Just one block from the beach!
A modern two-story house with a garage, a covered entryway, and a well-maintained lawn.

10. Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing

Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
Pebble Beach
9.6 out of 10, Exceptional, (4 reviews)
"The house was beautiful and lived up to the pictures. The hosts were responsive and very helpful during our stay. We were so happy to rent for a month and be able to bring our dog. Thank you so much!"
United States
Deborah M.
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
A covered outdoor area with a pool, lounge chairs, and a table with candles.

11. Villa Our Happy Place - Pool, Spa & Pets - Manasota

Villa Our Happy Place - Pool, Spa & Pets - Manasota
Englewood East
9.0 out of 10, Wonderful, (2 reviews)
"We love the locatio, pool, hot tub & fenced in yard were perfect for us!! Thank you!"
United States
Brenda B.
The price is AED 451
AED 1,714 total
includes taxes & fees
31 Oct - 1 Nov
Villa Our Happy Place - Pool, Spa & Pets - Manasota
A residential property with a paved driveway leading to a garage, surrounded by palm trees and a well-maintained lawn.

12. Lake Marlin Villa 2

Lake Marlin Villa 2
Englewood East
10.0 out of 10, Exceptional, (20 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
The price is AED 430
AED 820 total
includes taxes & fees
18 Nov - 19 Nov
Lake Marlin Villa 2
A table with a tray containing a cookie and two cups, set in a covered outdoor area with a view of a lake and greenery.

13. Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.6 out of 10, Exceptional, (17 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is AED 441
AED 832 total
includes taxes & fees
1 Nov - 2 Nov
Beautiful house with lake view
Pool

14. Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches

Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Englewood South
10.0 out of 10, Exceptional, (4 reviews)
"This was a wonderful vacation! The house was perfect! Very clean and decorated beautifully! We had everything that we needed! Great location too! We would recommend this house to anyone coming to Englewood, it was wonderful! We will be coming back! Thank you for sharing your beautiful house with us!!"
United States
Lisa M.
The price is AED 536
AED 1,568 total
includes taxes & fees
18 Nov - 19 Nov
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
A modern two-story house with a brick driveway and a well-maintained lawn.

15. Waterview Villa With Heated Pool

Waterview Villa With Heated Pool
Oakland Hills
10.0 out of 10, Exceptional, (1 review)
"Our host was very good at responding to our questions. The home was great! Very clean with everything you could need."
United States
Barbara H.
The price is AED 559
AED 1,500 total
includes taxes & fees
31 Oct - 1 Nov
Waterview Villa With Heated Pool
A pool area with lounge chairs and a blue umbrella.

16. The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen

The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
Port Charlotte
9.8 out of 10, Exceptional, (21 reviews)
"The house was great, the pool terrific. Our family enjoyed time together. Thank you."
United States
Marlo S.
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
A turquoise building with a tiled driveway and a row of bicycles parked in front.

17. Seaglass Inn at the Beach Shack Just one block from the beach!

Seaglass Inn at the Beach Shack Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (28 reviews)
"The Seaglass Inn was perfect for our weekend stay with the family. The location was great, and the place had everything we needed and then some. The beach was a quick walk away and beautiful! We would definitely book here again in the future. "
United States
erika b.
Seaglass Inn at the Beach Shack Just one block from the beach!
A turquoise two-story house with a covered porch, outdoor seating, and a small garden area.

18. Pineapple Express at the Beach Shack Just one block from the beach!

Pineapple Express at the Beach Shack Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (38 reviews)
"Everything you could want or need was available!Excellent location!Heather was amazing to work with!"
United States
lisa w.
Pineapple Express at the Beach Shack Just one block from the beach!
An indoor swimming pool with a clear view of the sky, a covered patio area, and a barbecue setup.

19. Massive Cali King Villa | Heated Saltwater Pool

Massive Cali King Villa | Heated Saltwater Pool
Pelican
9.6 out of 10, Exceptional, (24 reviews)
"100% recommended for a family vacation!"
United States
Tommy P.
The price is AED 364
AED 1,502 total
includes taxes & fees
2 Nov - 3 Nov
Massive Cali King Villa | Heated Saltwater Pool
A covered outdoor area with a pool, patio furniture, and a view of a resort.

20. Gulf access home, heated pool & kayaks

Gulf access home, heated pool & kayaks
Pelican
9.4 out of 10, Exceptional, (12 reviews)
"Good vibes"
United States
Alejandro A.
The price is AED 629
AED 1,994 total
includes taxes & fees
31 Oct - 1 Nov
Gulf access home, heated pool & kayaks
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gasparilla Island Hotel Reviews

The Suites at Fishermen’s Village

The Suites at Fishermen’s Village

10/10 Excellent
"The room was fantastic, food was amazing and fairly priced. Already booked another trip"
Troy 7-night trip
Posted 6 hours ago
The Suites at Fishermen’s Village

Frequently asked questions

Why book your villa in Gasparilla Island with Expedia?
We think planning a vacation shouldn't be difficult, so if you're searching for villas at the right price, Expedia is here to help. Save those pennies and select an all-inclusive stay, or splurge on a 5-star villa to spoil your favorite people. Our handy filters make it easy to find a place in Gasparilla Island that fits your needs.
How can I find cheap villas in Gasparilla Island?
With Expedia's useful filter tool, sourcing cheap villas in Gasparilla Island is a breeze. To discover properties that'll make your wallet smile, fine-tune your search by budget, star rating and amenities.

Explore a world of travel with Expedia