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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Gasparilla Island villas

Terrace/patio

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 ￥14,576
￥53,480 total
includes taxes & fees
Sep 15 - Sep 16
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Exterior

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 ￥18,291
￥58,275 total
includes taxes & fees
Sep 15 - Sep 16
Waterview Vacation Retreat Close To Ocean
Children's area

3. "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 ￥10,575
￥62,223 total
includes taxes & fees
Sep 12 - Sep 13
"Sea Cottage" 3 bedroom 2 bath cozy retreat with smart 65in TV
Exterior

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 ￥20,006
￥59,561 total
includes taxes & fees
Sep 4 - Sep 5
3BR Boundary Breeze Heated Pool Beach Golf Nearby
Exterior

5. 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 ￥26,761
￥57,452 total
includes taxes & fees
Sep 17 - Sep 18
Turtle Cay at The Beach Shack! Come On Down!
Exterior

6. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (296 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 ￥21,007
￥35,332 total
includes taxes & fees
Sep 9 - Sep 10
Matlacha Tiny Village
Exterior

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 ￥12,385
￥63,773 total
includes taxes & fees
Sep 4 - Sep 5
"Sea Dunes" 3 bedrooms 2 bath
Exterior

8. 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 ￥15,402
￥51,832 total
includes taxes & fees
Sep 13 - Sep 14
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
Exterior

9. 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 ￥26,761
￥59,039 total
includes taxes & fees
Oct 4 - Oct 5
Seashell Shanty at The Beach Shack! Come On Down!
Exterior

10. Lake Marlin Villa 2

Lake Marlin Villa 2
Englewood East
10.0 out of 10, Exceptional, (16 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
The price is ￥18,577
￥35,287 total
includes taxes & fees
Sep 20 - Sep 21
Lake Marlin Villa 2
Exterior

11. 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 ￥26,761
￥58,722 total
includes taxes & fees
Sep 13 - Sep 14
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Outdoor pool, a heated pool

12. 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 ￥35,583
￥104,795 total
includes taxes & fees
Sep 8 - Sep 9
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
Outdoor pool, a heated pool

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 ￥23,086
￥70,012 total
includes taxes & fees
Sep 30 - Oct 1
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Exterior

14. 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 ￥38,542
￥79,234 total
includes taxes & fees
Sep 8 - Sep 9
Seaglass Inn at the Beach Shack Just one block from the beach!
Exterior

15. 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 ￥38,542
￥79,234 total
includes taxes & fees
Sep 7 - Sep 8
Pineapple Express at the Beach Shack Just one block from the beach!
Exterior

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 ￥21,435
￥62,273 total
includes taxes & fees
Sep 17 - Sep 18
Waterview Villa With Heated Pool
Indoor pool, a heated pool

17. Massive Cali King Villa | Heated Saltwater Pool

Massive Cali King Villa | Heated Saltwater Pool
Pelican
9.6 out of 10, Exceptional, (18 reviews)
"Our stay was great. Beautiful property, clean, and well stocked with everything as described. "
United States
Virginia W.
The price is ￥16,434
￥66,348 total
includes taxes & fees
Sep 9 - Sep 10
Massive Cali King Villa | Heated Saltwater Pool
Outdoor pool, a heated pool

18. Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal View

Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal View
Trafalgar
9.4 out of 10, Exceptional, (32 reviews)
"House was clean and had everything we needed! Enjoyed our stay very much! Host was very responsive! We would recommended staying here."
United States
Samantha T.
The price is ￥36,440
￥114,345 total
includes taxes & fees
Sep 8 - Sep 9
Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal View
Terrace/patio

19. 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)
"This house was perfect for our family! The hosts thought of all the small details and were very communicative and responsive. We had a wonderful stay and look forward to returning!"
United States
Wendy P.
The price is ￥90,230
￥212,852 total
includes taxes & fees
Sep 22 - Sep 23
Multiple Families! 3 min walk to Beach, Jacuzzi, Heated Salt Wtr Pool, Game room
Exterior

20. Sweet Escape In The Cape

Sweet Escape In The Cape
Pelican
8.0 out of 10, Very Good, (5 reviews)
The price is ￥23,817
￥77,308 total
includes taxes & fees
Sep 8 - Sep 9
Sweet Escape In The Cape
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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

10/10 Excellent
"Great experience"
Eliovanis 3-night trip
Posted 12 hours ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Find out more about Gasparilla Island

Gasparilla Island Villas information

Number of reviews
711
Accommodation
136 Villas
Lowest Price
￥35,287
Highest Price
￥212,852

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