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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Gasparilla Island villas

An outdoor patio area with a seating arrangement, a hammock, and a view of a grassy yard and trees.

1. 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.
The price is ￥13,744
￥50,872 total
includes taxes & fees
Sep 20 - Sep 21
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
A residential area with a pond, palm trees, and houses with sloped roofs.

2. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (18 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is ￥14,577
￥51,959 total
includes taxes & fees
Sep 20 - Sep 21
Waterview Vacation Retreat Close To Ocean
A modern two-story house with a brick driveway and a well-maintained lawn.

3. 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 ￥17,770
￥55,842 total
includes taxes & fees
Sep 17 - Sep 18
3BR Boundary Breeze Heated Pool Beach Golf Nearby
A beachside area with colorful beach houses, a dock, and a sandy beach.

4. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 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 ￥20,407
￥34,323 total
includes taxes & fees
Sep 21 - Sep 22
Matlacha Tiny Village
A playground with slides and climbing structures, surrounded by a lake and palm trees.

5. "Sea Cottage" 3 bedroom 2 bath cozy retreat with smart 65in TV

"Sea Cottage" 3 bedroom 2 bath cozy retreat with smart 65in TV
Port Charlotte
9.4 out of 10, Exceptional, (3 reviews)
"Clean and well equipped "
United States
Deb H.
The price is ￥10,332
￥59,241 total
includes taxes & fees
Sep 25 - Sep 26
"Sea Cottage" 3 bedroom 2 bath cozy retreat with smart 65in TV
A modern two-story house with a garage, a covered entryway, and a well-maintained lawn.

6. 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 ￥14,295
￥49,798 total
includes taxes & fees
Sep 17 - Sep 18
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
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 ￥12,032
￥60,565 total
includes taxes & fees
Sep 18 - Sep 19
"Sea Dunes" 3 bedrooms 2 bath
A covered patio with a table and chairs, a wooden fence, and a view of a backyard with a barbecue grill.

8. 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)
"Yes everything was great had a wonderful time "
United States
Melinda M.
The price is ￥25,997
￥54,115 total
includes taxes & fees
Sep 20 - Sep 21
Turtle Cay at The Beach Shack! Come On Down!
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.

9. Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.6 out of 10, Exceptional, (16 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is ￥20,787
￥37,895 total
includes taxes & fees
Sep 20 - Sep 21
Beautiful house with lake view
A two-story building with a sign reading 'Beach Shack.'

10. 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)
The price is ￥26,146
￥57,217 total
includes taxes & fees
Sep 27 - Sep 28
Seashell Shanty at The Beach Shack! Come On Down!
A residential property with a paved driveway leading to a garage, surrounded by palm trees and a well-maintained lawn.

11. Lake Marlin Villa 2

Lake Marlin Villa 2
Englewood East
10.0 out of 10, Exceptional, (17 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
The price is ￥18,150
￥34,476 total
includes taxes & fees
Sep 20 - Sep 21
Lake Marlin Villa 2
A turquoise building with a tiled driveway and a row of bicycles parked in front.

12. 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 ￥25,997
￥56,583 total
includes taxes & fees
Sep 20 - Sep 21
Flamingo's Nest at the Beach Shack. Just one block from the beach!

13. 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 ￥21,842
￥65,356 total
includes taxes & fees
Sep 30 - Oct 1
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
A pool area with lounge chairs and a blue umbrella.

14. 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 ￥34,765
￥101,300 total
includes taxes & fees
Sep 17 - Sep 18
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
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 ￥18,150
￥56,628 total
includes taxes & fees
Sep 17 - Sep 18
Waterview Villa With Heated Pool
A coastal resort area with multiple buildings, including a prominent hotel with a red roof and a parking lot.

16. 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 ￥37,443
￥77,437 total
includes taxes & fees
Sep 22 - Sep 23
Pineapple Express at the Beach Shack Just one block from the beach!
A coastal resort area with multiple buildings, including a prominent hotel with a red roof and a parking lot.

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.
The price is ￥37,656
￥74,776 total
includes taxes & fees
Sep 17 - Sep 18
Seaglass Inn 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.

18. Massive Cali King Villa | Heated Saltwater Pool

Massive Cali King Villa | Heated Saltwater Pool
Pelican
9.6 out of 10, Exceptional, (19 reviews)
"Our stay was great. Beautiful property, clean, and well stocked with everything as described. "
United States
Virginia W.
The price is ￥16,754
￥65,600 total
includes taxes & fees
Sep 21 - Sep 22
Massive Cali King Villa | Heated Saltwater Pool
A covered outdoor swimming pool with a view of a residential area.

19. Gulf Access Retreat with Heated Pool

Gulf Access Retreat with Heated Pool
Pelican
9.4 out of 10, Exceptional, (12 reviews)
"Perfect waterfront home, beautiful sunsets and sunrises. New favorite home."
United States
Brett B.
The price is ￥14,500
￥68,494 total
includes taxes & fees
Sep 20 - Sep 21
Gulf Access Retreat with Heated Pool

20. Multiple Families! 3 min walk to Beach, Jacuzzi, Heated Salt Wtr Pool, Game room

Multiple Families! 3 min walk to Beach, Jacuzzi, Heated Salt Wtr Pool, Game room
Manasota Key
10.0 out of 10, Exceptional, (8 reviews)
"Very nice place, lots of room for our family. Game room was very popular. We didn't use the hot tub but the pool was great. We went to several different beaches and found lots of sharks' teeth. All had a great time!"
United States
Bill O.
The price is ￥86,857
￥199,325 total
includes taxes & fees
Sep 21 - Sep 22
Multiple Families! 3 min walk to Beach, Jacuzzi, Heated Salt Wtr Pool, Game room
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 Gasparilla Island Hotel Reviews

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

8/10 Good
"Everything was great, except they reception didn't explai"
Andrew 2-night trip
Posted 18 hours ago
Wyvern Hotel, an Ascend Collection Hotel

Find out more about Gasparilla Island

Gasparilla Island Villas information

Number of reviews
408
Accommodation
136 Villas
Lowest Price
￥34,323
Highest Price
￥199,325

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