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

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 £249
includes taxes & fees
21 Sept - 22 Sept
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Exterior

2. 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 £166
includes taxes & fees
21 Sept - 22 Sept
Matlacha Tiny Village
Exterior

3. 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 £254
includes taxes & fees
21 Sept - 22 Sept
Waterview Vacation Retreat Close To Ocean
Children’s area

4. "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 £297
includes taxes & fees
25 Sept - 26 Sept
"Sea Cottage" 3 bedroom 2 bath cozy retreat with smart 65in TV
Exterior

5. 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 £273
includes taxes & fees
21 Sept - 22 Sept
3BR Boundary Breeze Heated Pool Beach Golf Nearby
Exterior

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 £247
includes taxes & fees
21 Sept - 22 Sept
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
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 £303
includes taxes & fees
21 Sept - 22 Sept
"Sea Dunes" 3 bedrooms 2 bath
Outdoor dining

8. 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 £185
includes taxes & fees
21 Sept - 22 Sept
Beautiful house with lake view
Outdoor dining

9. 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 £284
includes taxes & fees
21 Sept - 22 Sept
Turtle Cay 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, (18 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
The price is £168
includes taxes & fees
21 Sept - 22 Sept
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 £284
includes taxes & fees
21 Sept - 22 Sept
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 £492
includes taxes & fees
21 Sept - 22 Sept
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 £331
includes taxes & fees
30 Sept - 1 Oct
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Property grounds

14. 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 £284
includes taxes & fees
27 Sept - 28 Sept
Seashell Shanty at The Beach Shack! Come On Down!
Exterior

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 £276
includes taxes & fees
21 Sept - 22 Sept
Waterview Villa With Heated Pool
Indoor pool, a heated pool

16. 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 £317
includes taxes & fees
21 Sept - 22 Sept
Massive Cali King Villa | Heated Saltwater Pool
Exterior

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 £381
includes taxes & fees
21 Sept - 22 Sept
Seaglass Inn at the Beach Shack Just one block from the beach!
Pool

18. 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 £335
includes taxes & fees
21 Sept - 22 Sept
Gulf Access Retreat with Heated Pool
Exterior

19. 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 £381
includes taxes & fees
21 Sept - 22 Sept
Pineapple Express at the Beach Shack Just one block from the beach!
Outdoor pool, a heated pool

20. 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, (33 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 £560
includes taxes & fees
6 Oct - 7 Oct
Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal View
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
"Everything is good"
DIANELYS 3-night trip
Posted 6 hours ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Find out more about Gasparilla Island

Gasparilla Island Villas information

Number of reviews
416
Accommodation
135 Villas
Lowest Price
£166
Highest Price
£560

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