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

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 €293
includes taxes & fees
9 Sept - 10 Sept
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 €315
includes taxes & fees
16 Sept - 17 Sept
Waterview Vacation Retreat Close To Ocean
A playground with slides and climbing structures, surrounded by a lake and palm trees.

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 €341
includes taxes & fees
12 Sept - 13 Sept
"Sea Cottage" 3 bedroom 2 bath cozy retreat with smart 65in TV
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 €330
includes taxes & fees
16 Sept - 17 Sept
3BR Boundary Breeze Heated Pool Beach Golf Nearby
A residential area with houses, a beach, and a sunset.

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 €316
includes taxes & fees
13 Sept - 14 Sept
Turtle Cay at The Beach Shack! Come On Down!
A beachside area with colorful beach houses, a dock, and a sandy beach.

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 €192
includes taxes & fees
12 Sept - 13 Sept
Matlacha Tiny Village
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 €357
includes taxes & fees
4 Sept - 5 Sept
"Sea Dunes" 3 bedrooms 2 bath
A modern two-story house with a garage, a covered entryway, and a well-maintained lawn.

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 €285
includes taxes & fees
11 Sept - 12 Sept
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
An aerial view of a building with a flat roof, surrounded by a landscaped area with trees and a paved walkway.

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 €329
includes taxes & fees
10 Sept - 11 Sept
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.

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 €198
includes taxes & fees
20 Sept - 21 Sept
Lake Marlin Villa 2
A turquoise building with a tiled driveway and a row of bicycles parked in front.

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 €329
includes taxes & fees
10 Sept - 11 Sept
Flamingo's Nest at the Beach Shack. Just one block from the beach!
A pool area with lounge chairs and a blue umbrella.

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

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 €357
includes taxes & fees
1 Oct - 2 Oct
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
A coastal resort area with multiple buildings, including a prominent hotel with a red roof and a parking lot.

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.
Seaglass Inn 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.

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.
Pineapple Express 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 €340
includes taxes & fees
16 Sept - 17 Sept
Waterview Villa With Heated Pool
An indoor swimming pool with a clear view of the sky, a covered patio area, and a barbecue setup.

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 €344
includes taxes & fees
7 Sept - 8 Sept
Massive Cali King Villa | Heated Saltwater Pool
A swimming pool with a glass enclosure, surrounded by chairs and a view of the sky.

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

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 €1,146
includes taxes & fees
22 Sept - 23 Sept
Multiple Families! 3 min walk to Beach, Jacuzzi, Heated Salt Wtr Pool, Game room
A residential house with a garage, a well-maintained lawn, and palm trees.

20. Sweet Escape In The Cape

Sweet Escape In The Cape
Pelican
8.0 out of 10, Very good, (5 reviews)
"The house is amazing and and the location is close to beaches, restaurants, shopping etc. The layout of the house perfect and worked for all of our family. The only thing we had some problems with is the house was not stocked well, 4 towels for 6 people did not work well, also the master bathroom had ants everywhere and the shower still had hair in it. The TV on the patio kept shutting off after 4 minutes.The Air-conditioning went out as well while we were there (not their fault) but...
United States
Erna M.
The price is €442
includes taxes & fees
7 Sept - 8 Sept
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
135 Villas
Lowest Price
€192
Highest Price
€1,146

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