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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
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 HK$975
HK$1,675 total
includes taxes & fees
15 Oct - 16 Oct
Matlacha Tiny Village
A beach shack with a sign reading 'BEACH SHACK MANASOTA KEY,' a bicycle parked outside, and a chair and table set up for outdoor dining.

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 HK$1,323
HK$2,894 total
includes taxes & fees
3 Nov - 4 Nov
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)
"Nice stay in good location"
United States
John W.
The price is HK$699
HK$2,612 total
includes taxes & fees
15 Oct - 16 Oct
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
A residential area with a pond, palm trees, and houses with sloped roofs.

4. 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 HK$798
HK$2,730 total
includes taxes & fees
15 Oct - 16 Oct
Waterview Vacation Retreat Close To Ocean
A backyard with a gravel patio, a small lawn, and a wooden fence.

5. 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 HK$1,323
HK$2,894 total
includes taxes & fees
27 Oct - 28 Oct
Seashell Shanty at The Beach Shack! Come On Down!
A modern two-story house with a brick driveway and a well-maintained lawn.

6. 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 HK$904
HK$2,864 total
includes taxes & fees
15 Oct - 16 Oct
3BR Boundary Breeze Heated Pool Beach Golf Nearby
A turquoise building with a tiled driveway and a row of bicycles parked in front.

7. 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 HK$1,323
HK$2,879 total
includes taxes & fees
27 Oct - 28 Oct
Flamingo's Nest at the Beach Shack. Just one block from the beach!
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.

8. 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 HK$855
HK$1,674 total
includes taxes & fees
15 Oct - 16 Oct
Beautiful house with lake view
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, (19 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
The price is HK$777
HK$1,578 total
includes taxes & fees
14 Oct - 15 Oct
Lake Marlin Villa 2
A single-story house with a flat roof, large windows, and a small porch area.

10. "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 HK$549
HK$3,074 total
includes taxes & fees
14 Oct - 15 Oct
"Sea Dunes" 3 bedrooms 2 bath
A modern two-story house with a garage, a covered entryway, and a well-maintained lawn.

11. 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 HK$1,059
HK$2,943 total
includes taxes & fees
14 Oct - 15 Oct
Charming 3-bedroom Relaxing Family Vacation Retreat On The Water, Fishing
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 HK$1,148
HK$3,441 total
includes taxes & fees
28 Oct - 29 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.

13. 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 HK$1,905
HK$3,767 total
includes taxes & fees
8 Nov - 9 Nov
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.

14. 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 HK$1,905
HK$3,767 total
includes taxes & fees
8 Nov - 9 Nov
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.

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 HK$1,059
HK$3,054 total
includes taxes & fees
20 Oct - 21 Oct
Waterview Villa With Heated Pool
A pool area with lounge chairs and a blue umbrella.

16. 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 HK$2,550
HK$6,160 total
includes taxes & fees
21 Oct - 22 Oct
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
Terrace/patio

17. Fits Multiple Families! 3 min walk to Gulf, Hot Tub, Salt Water Pool, Game room

Fits Multiple Families! 3 min walk to Gulf, Hot Tub, Salt Water Pool, Game room
Manasota Key
10.0 out of 10, Exceptional, (10 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 HK$4,026
HK$9,820 total
includes taxes & fees
25 Oct - 26 Oct
Fits Multiple Families! 3 min walk to Gulf, Hot Tub, Salt Water Pool, Game room
A covered outdoor swimming pool with a view of a residential area.

18. Gulf access home, heated pool & kayaks

Gulf access home, heated pool & kayaks
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 HK$738
HK$3,477 total
includes taxes & fees
14 Oct - 15 Oct
Gulf access home, heated pool & kayaks
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, (22 reviews)
"Our stay was great. Beautiful property, clean, and well stocked with everything as described. "
United States
Virginia W.
The price is HK$848
HK$3,295 total
includes taxes & fees
18 Oct - 19 Oct
Massive Cali King Villa | Heated Saltwater Pool
A swimming pool with a glass enclosure, surrounded by chairs and a view of the sky.

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

Hot Tub & Private Pool · Screened Lanai · Game Room · BBQ · Canal View
Trafalgar
9.2 out of 10, Wonderful, (35 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 HK$2,084
HK$6,006 total
includes taxes & fees
3 Nov - 4 Nov
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

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

8/10 Good
"Walkable location. Friendly and helpful staff."
Tracey 4-night trip
Posted less than an hour ago
Wyvern Hotel, an Ascend Collection Hotel

Find out more about Gasparilla Island

Gasparilla Island Villas information

Number of reviews
432
Accommodation
136 Villas
Lowest Price
HK$1,578
Highest Price
HK$9,820

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