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

Holiday Homes 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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Gasparilla Island holiday homes

Living area

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is NZ$385
includes taxes & fees
5 July - 6 July
Nestled in North Port. Updated 2 Bed / 1 Bath.
Smart TV, stereo

Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (67 reviews)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
The price is NZ$418
includes taxes & fees
8 July - 9 July
Completely remodeled beautiful waterfront property on canal with dock
Fridge, microwave, oven, stovetop

Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.4 out of 10, Exceptional, (3 reviews)
"The house was very clean and well accommodating. There was room for our boat in the driveway. Will definitely stay again if in the area."
United States
Jeremy
The price is NZ$499
includes taxes & fees
7 July - 8 July
Path to Paradise.
Outdoor dining

Luxe 3BR Waterfront Stay in Cape Coral

Luxe 3BR Waterfront Stay in Cape Coral
Mariner
10.0 out of 10, Exceptional, (12 reviews)
"We were pleased with our stay. "
United States
Jamie G.
The price is NZ$591
includes taxes & fees
6 July - 7 July
Luxe 3BR Waterfront Stay in Cape Coral
Fridge, microwave, oven, stovetop

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
10.0 out of 10, Exceptional, (25 reviews)
"Ammenities were great.Everything you need.Bring a carry on and check inWill stay again."
United States
Keenan F.
The price is NZ$563
includes taxes & fees
7 July - 8 July
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Sun-loungers

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (3 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is NZ$428
includes taxes & fees
11 July - 12 July
Charming 2-bedroom house in Englewood with WiFi and AC
Exterior

Amazing Waterfront House with Heated Pool near Hospitals

Amazing Waterfront House with Heated Pool near Hospitals
Port Charlotte
The price is NZ$868
includes taxes & fees
5 July - 6 July
Amazing Waterfront House with Heated Pool near Hospitals
Fridge, microwave, oven, stovetop

Myakka River

Myakka River
Venice
10.0 out of 10, Exceptional, (21 reviews)
"Very clean property. Great outdoor space. Very quiet and relaxing area. Would definitely stay again. "
United States
Tom D.
The price is NZ$764
includes taxes & fees
5 July - 6 July
Myakka River
Interior

Harbor House, renovated luxury waterfront- 30 ft private dock

Harbor House, renovated luxury waterfront- 30 ft private dock
Edgewater
9.8 out of 10, Exceptional, (28 reviews)
"We had a great stay. Very clean home with new comforts!"
United States
Robert D.
The price is NZ$808
includes taxes & fees
6 July - 7 July
Harbor House, renovated luxury waterfront- 30 ft private dock
Dining

Charming & Cozy: Close to Beach & Shops ~ Parking!

Charming & Cozy: Close to Beach & Shops ~ Parking!
Port Charlotte
9.4 out of 10, Exceptional, (6 reviews)
"We had a nice stay"
United States
Laurie A.
The price is NZ$383
includes taxes & fees
7 July - 8 July
Charming & Cozy: Close to Beach & Shops ~ Parking!
Fridge, microwave, oven, stovetop

2-bedroom pool house with golf cart in Englewood, close to the beaches!

2-bedroom pool house with golf cart in Englewood, close to the beaches!
Grove City
10.0 out of 10, Exceptional, (10 reviews)
The price is NZ$595
includes taxes & fees
6 July - 7 July
2-bedroom pool house with golf cart in Englewood, close to the beaches!
Interior

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Oakland Hills
10.0 out of 10, Exceptional, (14 reviews)
"Place was clean and nicely furnished. Would re-book. "
United States
kathleen g.
The price is NZ$590
includes taxes & fees
5 July - 6 July
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Sun-loungers, beach towels

NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (49 reviews)
"Great week spent at the Waterside Cottage! "
United States
Sandy S.
The price is NZ$692
includes taxes & fees
6 July - 7 July
NEW!! The “WATERSIDE” COTTAGE~With dockage
Dining

Waterfront Pool Home Canal Front in Quiet Area

Waterfront Pool Home Canal Front in Quiet Area
New York Section
8.8 out of 10, Excellent, (16 reviews)
"Awesome host and beautiful home."
United States
cheryl b.
The price is NZ$750
includes taxes & fees
5 July - 6 July
Waterfront Pool Home Canal Front in Quiet Area
Dining

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"The home was absolutely perfect , clean, spacious, and very comfortable. Beautifully decorated , beds were cozy, and everything was exactly as described. The host was friendly and responsive, which made the stay stress-free. Great location and a perfect home base for our family trip.”"
United States
Kelly R.
The price is NZ$747
includes taxes & fees
5 July - 6 July
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Beach nearby, beach towels

Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (7 reviews)
"Stayed here several times. Always perfect. Feels like home. "
United States
christine w.
The price is NZ$452
includes taxes & fees
6 July - 7 July
Nautical Nook
Outdoor dining

Venice Dove Shell

Venice Dove Shell
Venice East
9.8 out of 10, Exceptional, (9 reviews)
"Great place!!"
United States
Scot
The price is NZ$631
includes taxes & fees
6 July - 7 July
Venice Dove Shell
Terrace/patio

Sunshine Hideaway 6 mins to Warm Mineral Springs

Sunshine Hideaway 6 mins to Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (9 reviews)
"Very nice place with comfortable beds "
United States
Josh H.
The price is NZ$453
includes taxes & fees
6 July - 7 July
Sunshine Hideaway 6 mins to Warm Mineral Springs
Sun-loungers, beach towels

PLACE TO BE we have everything you need

PLACE TO BE we have everything you need
Warm Mineral Springs
8.8 out of 10, Excellent, (16 reviews)
"Great host "
United States
Brett W.
The price is NZ$527
includes taxes & fees
5 July - 6 July
PLACE TO BE we have everything you need
Fridge, microwave, oven, stovetop

3-bedroom house in marvelous Port Charlotte with AC comfort and heated pool.

3-bedroom house in marvelous Port Charlotte with AC comfort and heated pool.
Port Charlotte
10.0 out of 10, Exceptional, (3 reviews)
"This was a perfect spot for a staycation. The house is beautiful and the host was very responsive to my questions."
United States
Bradi M.
The price is NZ$793
includes taxes & fees
5 July - 6 July
3-bedroom house in marvelous Port Charlotte with AC comfort and 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

10/10 Excellent
"Great long weekend getaway, Lots of options to eat on property. Only knock if you like evening pool swims you will not get this here. Pool closes at sunset. Not much for kids to do, Great for a couple getaway"
Leticia 3-night trip
Posted 6 hours ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Find out more about Gasparilla Island

Gasparilla Island Holiday Homes information

Number of reviews
14,671
Accommodation
1239 Holiday Homes
Lowest Price
NZ$123
Highest Price
NZ$606

Explore a world of travel with Expedia