Photo by Brooke Csaky

Search Villas in Gasparilla Island

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Gasparilla Island villas

Villa in Matlacha

Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (268)
"Very nice place with all necesary accommodations for a Pleasant stay. "
United States
isabel
The price is ¥19,533
¥33,492 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Matlacha Tiny Village
9.8 out of 10, Exceptional, (60)
"We had a great time even the weather was bad we had an amazing time in the home play games and watch movies "
United States
Adam L.
The price is ¥27,367
¥63,868 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Villa in Englewood East

Beautiful house with lake view
10.0 out of 10, Exceptional, (10)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is ¥30,564
¥46,052 total
includes taxes & fees
Dec 30 - Dec 31
Beautiful house with lake view
10.0 out of 10, Exceptional, (43)
"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 ¥25,290
¥54,967 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Turtle Cay at The Beach Shack! Come On Down!
10.0 out of 10, Exceptional, (40)
"Location was great, property condition is excellent!"
United States
Mabel
The price is ¥25,456
¥55,471 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Flamingo's Nest at the Beach Shack. Just one block from the beach!

Villa in Englewood East

Lake Marlin Villa 2
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful and clean! My Wife and I really enjoyed our stay in this elegant and clean home and would not hesitate to book again when we are back in the area. "
United States
Murray G.
The price is ¥22,034
¥36,530 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lake Marlin Villa 2
9.8 out of 10, Exceptional, (10)
"The property was very nice well appointed. All communication with owner was prompt and courteous. Would definitely stay there again. "
United States
Kevin C.
The price is ¥21,754
¥56,802 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Waterview Vacation Retreat Close To Ocean
10.0 out of 10, Exceptional, (2)
"The house is spotlessly clean and beautifully decorated. Extremely comfortable with every possible amenity. Quiet neighborhood close to the beaches. The hosts were easily accessible. Top rating!! We will definitely return."
United States
Mark H.
The price is ¥30,128
¥73,341 total
includes taxes & fees
Jan 13 - Jan 14, 2026
❤️️Luxury Villa in Englewood, Private Pool 😎, Game Room, 6 mins to Beaches
10.0 out of 10, Exceptional, (7)
"Immaculate and cozy with a heated pool and gulf access. The available kayaks were a fantastic bonus!"
United States
Andrew M.
The price is ¥49,965
¥113,327 total
includes taxes & fees
Dec 28 - Dec 29
Gulf Access Retreat with Heated Pool
10.0 out of 10, Exceptional, (24)
"It was very clean, very nice place with tons to offer."
United States
Zac I.
The price is ¥34,547
¥70,263 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Seaglass Inn at the Beach Shack Just one block from the beach!
9.8 out of 10, Exceptional, (15)
"We were in town for a wedding near by! The house was a great place to relax between events!"
United States
Janet B.
The price is ¥50,746
¥122,258 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Ultimate Luxury 4 BR/3 BA, Heated Pool, Outdoor Kitchen
10.0 out of 10, Exceptional, (43)
"We had a wonderful experience. We 100% recommend this property and hosts. "
United States
Christian S.
The price is ¥33,225
¥66,303 total
includes taxes & fees
Dec 30 - Dec 31
Seashell Shanty at The Beach Shack! Come On Down!

Villa in Pelican

Villa Aviator
8.0 out of 10, Very Good, (3)
"Great property "
United States
Ícaro
The price is ¥42,728
¥119,140 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa Aviator
The price is ¥23,421
¥75,072 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish salt water pool home is ideal for a respectable holiday

Villa in Port Charlotte

"Sea Dunes" 3 bedrooms 2 bath
The price is ¥23,157
¥75,414 total
includes taxes & fees
Jan 1 - Jan 2, 2026
"Sea Dunes" 3 bedrooms 2 bath

Villa in Pelican

Sweet Escape In The Cape
7.4 out of 10, Good, (3)
"We had a great time utilizing this vacation rental in order to be close to our other family, a road over. The propane tank was empty so we got a brand new one for the grill. The property itself was great. The bedrooms had nice decor. The kitchen was spacious and clean. The pool area was perfect for swimming and lounging. Everything worked as it should. "
United States
lyndsey b.
The price is ¥28,574
¥82,861 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Sweet Escape In The Cape
3.0 star property
The price is ¥30,938
¥73,634 total
includes taxes & fees
Jan 3 - Jan 4, 2026
3BR Boundary Breeze Heated Pool Beach Golf Nearby

Villa in Burnt Store

Luxurious Golf Villa
9.0 out of 10, Wonderful, (9)
"Property was clean and stay was very enjoyable !"
United States
Lisa S.
The price is ¥41,402
¥105,362 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Luxurious Golf Villa
10.0 out of 10, Exceptional, (37)
"Great place with snacks!"
United States
Nancy N.
The price is ¥34,547
¥72,603 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Pineapple Express at the Beach Shack Just one block from the beach!
9.2 out of 10, Wonderful, (17)
"Very nice, clean, and conveniently located vacation home. Pool was great and clean and the hot tub was a nice bonus. Rooms are large and very nucely decorated. The entire family had a great time."
United States
Dennis S.
The price is ¥53,868
¥153,709 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Gasparilla Island Hotel Reviews

Find out more about Gasparilla Island

Gasparilla Island Villas information

Number of reviews
564
Accommodation
125 Villas
Lowest Price
¥33,492
Highest Price
¥153,709

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.

Explore a world of travel with Expedia