A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

Search Villas in Gasparilla Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Gasparilla Island villas

Exterior

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (292 reviews)
"Very nice alternative to a motel quite clean everything you need for your stay. highly recommend this property"
United States
PETER
The price is AED 404
AED 726 total
includes taxes & fees
14 Jul - 15 Jul
Matlacha Tiny Village
Outdoor pool, a heated pool

Luxurious Golf Villa

Luxurious Golf Villa
Burnt Store
9.0 out of 10, Wonderful, (9 reviews)
"Excellent property with excellent host! Would definitely stay here again!"
United States
Chad N.
The price is AED 909
AED 2,415 total
includes taxes & fees
13 Jul - 14 Jul
Luxurious Golf Villa
Exterior detail

Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool

Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
North Port
10.0 out of 10, Exceptional, (11 reviews)
The price is AED 955
AED 2,603 total
includes taxes & fees
13 Jul - 14 Jul
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
Outdoor pool, a heated pool

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)
"Pool was very nice water was warm, needs blinds curtains on front door very nice house with 4 nice beds 3 baths and 30 to Atlanta Braves Stadium"
United States
Douglas D.
The price is AED 1,084
AED 2,727 total
includes taxes & fees
12 Aug - 13 Aug
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
TV

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, (46 reviews)
"Yes everything was great had a wonderful time "
United States
Melinda M.
The price is AED 619
AED 1,347 total
includes taxes & fees
6 Aug - 7 Aug
Turtle Cay at The Beach Shack! Come On Down!
Terrace/patio

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, (75 reviews)
"Nice stay in good location"
United States
John W.
The price is AED 384
AED 1,179 total
includes taxes & fees
19 Jul - 20 Jul
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Outdoor dining

Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.6 out of 10, Exceptional, (15 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is AED 492
AED 901 total
includes taxes & fees
20 Jul - 21 Jul
Beautiful house with lake view
Exterior

Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (17 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is AED 497
AED 1,317 total
includes taxes & fees
13 Jul - 14 Jul
Waterview Vacation Retreat Close To Ocean
Terrace/patio

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, (43 reviews)
"Wonderful place and a great location "
United States
Matthew C.
The price is AED 619
AED 1,358 total
includes taxes & fees
15 Jul - 16 Jul
Seashell Shanty at The Beach Shack! Come On Down!
Exterior

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 rental was excellent. A well stocked kitchen and everything you need for the beach. The walk to the beach is very short and convenient. We will be back. Highly recommend. "
United States
Roxanne D.
The price is AED 775
AED 1,628 total
includes taxes & fees
12 Aug - 13 Aug
Seaglass Inn at the Beach Shack Just one block from the beach!
Outdoor pool, a heated pool

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 496
AED 1,542 total
includes taxes & fees
12 Aug - 13 Aug
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Exterior

Lake Marlin Villa 2

Lake Marlin Villa 2
Englewood East
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
Lake Marlin Villa 2
Outdoor pool, a heated pool

Pet friendly spacious home for large groups! Pool & jacuzzi, game room!

Pet friendly spacious home for large groups! Pool & jacuzzi, game room!
Trafalgar
9.4 out of 10, Exceptional, (27 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 992
AED 2,818 total
includes taxes & fees
15 Jul - 16 Jul
Pet friendly spacious home for large groups! Pool & jacuzzi, game room!
Exterior

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)
"Great place with snacks!"
United States
Nancy N.
The price is AED 775
AED 1,636 total
includes taxes & fees
12 Aug - 13 Aug
Pineapple Express at the Beach Shack Just one block from the beach!
Exterior

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 1,366 total
includes taxes & fees
8 Aug - 9 Aug
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Property grounds

Modern Port Charlotte Retreat with Heated Pool

Modern Port Charlotte Retreat with Heated Pool
Port Charlotte
Modern Port Charlotte Retreat with Heated Pool
Terrace/patio

Casa del Lago: Relaxing Waterfront Pool House

Casa del Lago: Relaxing Waterfront Pool House
Mariner
The price is AED 1,286
AED 2,401 total
includes taxes & fees
20 Jul - 21 Jul
Casa del Lago: Relaxing Waterfront Pool House
Exterior

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 621
AED 1,573 total
includes taxes & fees
12 Aug - 13 Aug
Waterview Villa With Heated Pool
Exterior

"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 1,486 total
includes taxes & fees
13 Jul - 14 Jul
"Sea Dunes" 3 bedrooms 2 bath
Pool

Gulf Access Retreat with Heated Pool

Gulf Access Retreat with Heated Pool
Pelican
9.4 out of 10, Exceptional, (11 reviews)
"Immaculate and cozy with a heated pool and gulf access. The available kayaks were a fantastic bonus!"
United States
Andrew M.
The price is AED 474
AED 1,802 total
includes taxes & fees
23 Jul - 24 Jul
Gulf Access Retreat with Heated Pool
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gasparilla Island Hotel Reviews

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

8/10 Good
"Room was clean Staff was friendly Outdoor pool lounge chairs were showing age and some appeared dirty with what appeared as mold"
Joseph 3-night trip
Posted 1 hour ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Frequently asked questions

Why book your villa in Gasparilla Island with Expedia?
We think planning a vacation shouldn't be difficult, so if you're searching for villas at the right price, Expedia is here to help. Save those pennies and select an all-inclusive stay, or splurge on a 5-star villa to spoil your favorite people. Our handy filters make it easy to find a place in Gasparilla Island that fits your needs.
How can I find cheap villas in Gasparilla Island?
With Expedia's useful filter tool, sourcing cheap villas in Gasparilla Island is a breeze. To discover properties that'll make your wallet smile, fine-tune your search by budget, star rating and amenities.