Search Villas in Gasparilla Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Villas in Gasparilla Island

Charming waterfront pool villa
Property grounds

Charming waterfront pool villa

Charming waterfront pool villa
Sweet Escape In The Cape
Outdoor pool, a heated pool

Sweet Escape In The Cape

7.4 out of 10, Good, (3)
"We booked this prop early Jan and got confirmations but a no communication back until the day of check in and found out Vrbo booked the same property to someone else on airb&b. So no place to stay for the family and was 10 min out to arrival. We had to sit in a parking lot for a couple of hours trying to find another place open! Vrbo didn’t help us find another place and gave us just two nights hotel stay and was limited amount. Asked to speak with a manger several times and got hung up on once...
Sweet Escape In The Cape
Villa Aviator
An infinity pool, a heated pool

Villa Aviator

8.0 out of 10, Very good, (3)
"Great property "
Villa Aviator
Casa del Lago: Relaxing Waterfront Pool House
Pool

Casa del Lago: Relaxing Waterfront Pool House

Casa del Lago: Relaxing Waterfront Pool House
Newly Renovated, Sleeps 8, Pool, Game Room, Darts, Pool table, BBQ
Smart TV, video games

Newly Renovated, Sleeps 8, Pool, Game Room, Darts, Pool table, BBQ

The price is NZ$895
includes taxes & fees
17 Sept - 18 Sept
Newly Renovated, Sleeps 8, Pool, Game Room, Darts, Pool table, BBQ
Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!
Outdoor pool, a heated pool

Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!

9.4 out of 10, Exceptional, (16)
"The home was very spacious, clean, and comfortable. The neighborhood was pretty quiet and near some shops and eateries which was convenient. Host, Nataliya was very responsive and accommodated a special request. We enjoyed our stay and look forward to returning in the near future."
The price is NZ$1,469
includes taxes & fees
19 Aug - 20 Aug
Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!
Waterfront,GulfAccess, Htd Pool/Spa, Family Friendly Getaway
A heated pool, pool umbrellas

Waterfront,GulfAccess, Htd Pool/Spa, Family Friendly Getaway

9.4 out of 10, Exceptional, (10)
"we enjoyed our stay. "
Waterfront,GulfAccess, Htd Pool/Spa, Family Friendly Getaway
Massive Cali King Villa | Heated Saltwater Pool
Indoor pool, a heated pool

Massive Cali King Villa | Heated Saltwater Pool

9.0 out of 10, Wonderful, (6)
"Spacious home, so many ammenities,Would come again!"
The price is NZ$812
includes taxes & fees
19 Aug - 20 Aug
Massive Cali King Villa | Heated Saltwater Pool
The Twins Villa
A heated pool

The Twins Villa

9.6 out of 10, Exceptional, (12)
"My daughter and her family had a great time everything was great"
The price is NZ$1,196
includes taxes & fees
15 Sept - 16 Sept
The Twins Villa
Luxurious Golf Villa
Outdoor pool, a heated pool

Luxurious Golf Villa

9.0 out of 10, Wonderful, (9)
"Excellent property with excellent host! Would definitely stay here again!"
The price is NZ$1,129
includes taxes & fees
19 Aug - 20 Aug
Luxurious Golf Villa
Matlacha Tiny Village
Dock

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (263)
"Very nice place with all necesary accommodations for a Pleasant stay. "
The price is NZ$311
includes taxes & fees
19 Aug - 20 Aug
Matlacha Tiny Village
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
Sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (7)
"Very relaxing..very spacious..decor was outstanding..very clean .and inviting..love it"
The price is NZ$1,336
includes taxes & fees
19 Aug - 20 Aug
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
Experience The Ultimate Luxury: 4 BR/3 BA, Heated Pool, Lanai, Fire Pit
Outdoor pool

Experience The Ultimate Luxury: 4 BR/3 BA, Heated Pool, Lanai, Fire Pit

9.8 out of 10, Exceptional, (15)
"Everything was as pictured and described. Location is just off a busy road, traffic loud at times when sitting outside. "
The price is NZ$1,439
includes taxes & fees
19 Aug - 20 Aug
Experience The Ultimate Luxury: 4 BR/3 BA, Heated Pool, Lanai, Fire Pit
"Sea Dunes" 3 bedrooms 2 bath
Sun-loungers, beach towels

"Sea Dunes" 3 bedrooms 2 bath

The price is NZ$730
includes taxes & fees
19 Aug - 20 Aug
"Sea Dunes" 3 bedrooms 2 bath
Beautiful house with lake view
Outdoor dining

Beautiful house with lake view

10.0 out of 10, Exceptional, (10)
"This villa was so cozy and accommodating for my family! They had everything we needed for our stay and much more!"
The price is NZ$363
includes taxes & fees
18 Sept - 19 Sept
Beautiful house with lake view
Pet Friendly Canal Front 3-Bedroom Grand Villa with Pool, Linai and Dock
Pool

Pet Friendly Canal Front 3-Bedroom Grand Villa with Pool, Linai and Dock

2.0 star property
10.0 out of 10, Exceptional, (5)
"I really enjoyed the house and location. "
The price is NZ$861
includes taxes & fees
19 Aug - 20 Aug
Pet Friendly Canal Front 3-Bedroom Grand Villa with Pool, Linai and Dock
This stylish place is ideal for a respectable holiday quiet and cozy
Outdoor pool

This stylish place is ideal for a respectable holiday quiet and cozy

The price is NZ$769
includes taxes & fees
19 Aug - 20 Aug
This stylish place is ideal for a respectable holiday quiet and cozy
YOUR PRIVATE OASIS WITH POOL HEATER, MINUTES FROM THE BEACH!
Fridge, microwave, oven, stovetop

YOUR PRIVATE OASIS WITH POOL HEATER, MINUTES FROM THE BEACH!

10.0 out of 10, Exceptional, (27)
"Stayed here to be close to our family that lives in the area. House was easy to access and very clean with tons of nice touches. Will definitely stay here again!"
The price is NZ$690
includes taxes & fees
21 Aug - 22 Aug
YOUR PRIVATE OASIS WITH POOL HEATER, MINUTES FROM THE BEACH!
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Fridge, microwave, oven, stovetop

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

9.8 out of 10, Exceptional, (57)
"The home was clean, nicely appointed, in a nice neighborhood, and very convenient to local attractions."
The price is NZ$534
includes taxes & fees
19 Aug - 20 Aug
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Waterview Vacation Retreat Close To Ocean
Fridge, microwave, oven, stovetop

Waterview Vacation Retreat Close To Ocean

10.0 out of 10, Exceptional, (9)
"We stayed 2 weeks and this house was comfortable, had all the items we needed to cook, clean, and relax. It was a quick and easy drive to some really beautiful beaches and great restaurants! The host was easy to contact and responsive to our questions. Would absolutely book again! Perfect for our family and our dog. "
The price is NZ$565
includes taxes & fees
19 Aug - 20 Aug
Waterview Vacation Retreat Close To Ocean
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
Sign in
Sign up, it's free

Top Gasparilla Island Hotel Reviews

Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

10/10 Excellent
"We had a great time - everything we needed in one place so many options for dining, comfortable, clean rooms and a beautiful pool area with plenty of seating. Super fun for a long weekend. The staff was very customer focused. Would highly recommend."
Megan 3-night trip
Posted 2 days ago
Sunseeker Resort Charlotte Harbor