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 AED 327
AED 1,211 total
includes taxes & fees
17 Sep - 18 Sep
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 AED 347
AED 1,237 total
includes taxes & fees
15 Sep - 16 Sep
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 AED 245
AED 1,403 total
includes taxes & fees
27 Sep - 28 Sep
"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 AED 423
AED 1,330 total
includes taxes & fees
15 Sep - 16 Sep
3BR Boundary Breeze Heated Pool Beach Golf Nearby
Outdoor dining

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 AED 619
AED 1,289 total
includes taxes & fees
15 Sep - 16 Sep
Turtle Cay at The Beach Shack! Come On Down!
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 AED 356
AED 1,203 total
includes taxes & fees
15 Sep - 16 Sep
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 AED 286
AED 1,442 total
includes taxes & fees
20 Sep - 21 Sep
"Sea Dunes" 3 bedrooms 2 bath
Exterior

8. 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 AED 486
AED 817 total
includes taxes & fees
15 Sep - 16 Sep
Matlacha Tiny Village
Outdoor dining

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 AED 492
AED 897 total
includes taxes & fees
18 Sep - 19 Sep
Beautiful house with lake view
Exterior

10. 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 AED 430
AED 816 total
includes taxes & fees
20 Sep - 21 Sep
Lake Marlin Villa 2
Property grounds

11. 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 AED 619
AED 1,355 total
includes taxes & fees
27 Sep - 28 Sep
Seashell Shanty at The Beach Shack! Come On Down!
Exterior

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 AED 619
AED 1,347 total
includes taxes & fees
16 Sep - 17 Sep
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Outdoor pool, a heated pool

13. 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 AED 823
AED 2,398 total
includes taxes & fees
20 Sep - 21 Sep
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
Outdoor pool, a heated pool

14. 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 AED 444
AED 1,495 total
includes taxes & fees
5 Oct - 6 Oct
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
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 AED 430
AED 1,341 total
includes taxes & fees
15 Sep - 16 Sep
Waterview Villa With Heated Pool
Exterior

16. 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 AED 892
AED 1,844 total
includes taxes & fees
20 Sep - 21 Sep
Seaglass Inn at the Beach Shack Just one block from the beach!
Exterior

17. 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 AED 892
AED 1,844 total
includes taxes & fees
20 Sep - 21 Sep
Pineapple Express at the Beach Shack Just one block from the beach!
Indoor pool, a heated pool

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 AED 281
AED 1,410 total
includes taxes & fees
16 Sep - 17 Sep
Massive Cali King Villa | Heated Saltwater Pool
Pool

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 AED 345
AED 1,627 total
includes taxes & fees
22 Sep - 23 Sep
Gulf Access Retreat with Heated Pool
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 AED 909
AED 2,730 total
includes taxes & fees
15 Sep - 16 Sep
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

Dream Beach House, steps to the Beach and beautiful Sunsets

Dream Beach House, steps to the Beach and beautiful Sunsets

10/10 Excellent
" Una experiencia maravillosa!Nuestra estadía en esta hermosa casa de playa fue simplemente increíble. El lugar es precioso, acogedor, limpio y perfecto para disfrutar y relajarse. La ubicación es espectacular y hace que cada momento sea especial.Pero lo mejor de todo fueron los dueños. Son personas maravillosas, amables, atentos y siempre dispuestos a ayudar. Nos hicieron sentir como en casa desde el primer momento.Sin duda, recomendamos este lugar al 100%. ¡Estamos deseando volver! "
damaris l. 3-night trip
Posted 3 hours ago
Dream Beach House, steps to the Beach and beautiful Sunsets

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