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

Search Gasparilla Island Villa Rentals from CA $279

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

Our top choices for Gasparilla Island villas

A beachside area with colorful beach houses, a dock, and a sandy beach.

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 CA $185
CA $312 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $236
CA $517 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $150
CA $493 total
includes taxes & fees
Nov 1 - Nov 2
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.
The price is CA $201
CA $557 total
includes taxes & fees
Oct 29 - Oct 30
3BR Boundary Breeze Heated Pool Beach Golf Nearby
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.

5. 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 CA $140
CA $279 total
includes taxes & fees
Oct 29 - Oct 30
Beautiful house with lake view
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 CA $236
CA $517 total
includes taxes & fees
Oct 29 - Oct 30
Seashell Shanty at The Beach Shack! Come On Down!
A residential area with a pond, palm trees, and houses with sloped roofs.

7. 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 CA $177
CA $529 total
includes taxes & fees
Nov 1 - Nov 2
Waterview Vacation Retreat Close To Ocean
A two-story house with a well-maintained lawn and palm trees.

8. 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 CA $225
CA $764 total
includes taxes & fees
Oct 29 - Oct 30
Stunning Villa in Golfer's Paradise/Canal Views
A residential property with a paved driveway leading to a garage, surrounded by palm trees and a well-maintained lawn.

9. 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 CA $140
CA $279 total
includes taxes & fees
Oct 29 - Oct 30
Lake Marlin Villa 2
A turquoise building with a tiled driveway and a row of bicycles parked in front.

10. 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 CA $236
CA $517 total
includes taxes & fees
Oct 29 - Oct 30
Flamingo's Nest at the Beach Shack. Just one block from the beach!
A single-story house with a flat roof, large windows, and a small porch area.

11. "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 CA $98
CA $550 total
includes taxes & fees
Oct 29 - Oct 30
"Sea Dunes" 3 bedrooms 2 bath
Pool

12. 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 CA $204
CA $614 total
includes taxes & fees
Nov 18 - Nov 19
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
A modern two-story house with a garage, a covered entryway, and a well-maintained lawn.

13. 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.
The price is CA $189
CA $526 total
includes taxes & fees
Oct 29 - Oct 30
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.

14. Our Happy Place | Pool, Spa & Pets | Manasota

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 CA $172
CA $654 total
includes taxes & fees
Oct 29 - Oct 30
Our Happy Place | Pool, Spa & Pets | Manasota
A coastal resort area with multiple buildings, including a prominent hotel with a red roof and a parking lot.

15. 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.
The price is CA $325
CA $684 total
includes taxes & fees
Oct 29 - Oct 30
Seaglass Inn at the Beach Shack Just one block from the beach!
A modern two-story house with a brick driveway and a well-maintained lawn.

16. 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 CA $213
CA $572 total
includes taxes & fees
Oct 29 - Oct 30
Waterview Villa With Heated Pool
A coastal resort area with multiple buildings, including a prominent hotel with a red roof and a parking lot.

17. 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.
The price is CA $325
CA $684 total
includes taxes & fees
Nov 2 - Nov 3
Pineapple Express at the Beach Shack Just one block from the beach!
A pool area with lounge chairs and a blue umbrella.

18. 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 price is CA $350
CA $961 total
includes taxes & fees
Oct 29 - Oct 30
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
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 CA $139
CA $573 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $240
CA $761 total
includes taxes & fees
Oct 31 - Nov 1
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

Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

10/10 Excellent
"Excellent customer service. Outstanding value for the money. Great sheets and pillows. When other chains are gouging travelers while providing nothing more than Baymont. I didn’t eat the breakfast or swim in the pool. If you don’t mind having your door open to the outside of the building instead of a hallway, then definitely stay there!"
Stephen Burks 1-night trip
Posted 20 hours ago
Baymont by Wyndham Punta Gorda/Port Charlotte

Find out more about Gasparilla Island

Gasparilla Island Villas information

Number of reviews
402
Accommodation
135 Villas
Lowest Price
CA $279
Highest Price
CA $961

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