Gasparilla Island Holiday Rentals

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (960)
"Great stay"
The price is NZ$293
includes taxes & fees
28 Aug - 29 Aug
The Suites at Fishermen’s Village- 2 Bedroom Suites

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

9.6 out of 10, Exceptional, (97)
"Everything was perfect."
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

10.0 out of 10, Exceptional, (41)
"We had a wonderful time!"
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

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
18 Aug - 19 Aug
Matlacha Tiny Village

“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

10.0 out of 10, Exceptional, (5)
"This property is amazing! Beautiful views and great fishing right off the dock. My wife and I stayed for our belated anniversary and we couldnt have been happier. We will be back."
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

120 steps to beach! Safely on the beach side of the road!

9.8 out of 10, Exceptional, (181)
"House was nice and had great location!"
120 steps to beach! Safely on the beach side of the road!

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (11)
"Nic place to stay and enjoy the area"
The price is NZ$909
includes taxes & fees
17 Aug - 18 Aug
Chadwick Cove Resort & Marina

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (78)
"I loved the property and the host was also very professional. "
Paradise Cove at Lemon Bay

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.6 out of 10, Excellent, (14)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

9.0 out of 10, Wonderful, (18)
"We took our multigenerational family for a few days of quiet & sunshine. They loved the place so mush that they want to go back next year!We had a few problems with the house but the management team made it right.Lovely place to spend a few days - or more!"
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

Luxury GULF access! DOCK/SPA/Pool/GAME ROOM

10.0 out of 10, Exceptional, (22)
"Just a very welcoming home, making for an easy, relaxing spring break. Well maintained. Has all the amenities one could want or need. We felt very at home here. The kids were over the moon, being able to hang out and swim all day. Would book again!"
Luxury GULF access! DOCK/SPA/Pool/GAME ROOM

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.0 out of 10, Wonderful, (61)
"Loved our stay! "
The price is NZ$570
includes taxes & fees
19 Aug - 20 Aug
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

New luxury pool home, 2 min to beach, 360 water views, club available

9.8 out of 10, Exceptional, (108)
"Loved this Beach home! We had our entire family on this North Captiva trip, perfect beach house with pool, great space for everyone!! Close to all beaches with golf carts. Owners were awesome, fast replies! We could see the water from many rooms at the house!! Thank you!!"
New luxury pool home, 2 min to beach, 360 water views, club available

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

9.4 out of 10, Exceptional, (46)
"The atmosphere and art very local"
The price is NZ$263
includes taxes & fees
17 Aug - 18 Aug
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"Had a great family vacation. We spent lots of time on the beach & fishing off the dock. We were especially grateful for your turtle education thank you for letting us partake in that. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

8.0 out of 10, Very good, (18)
"Came up for a weekend get away with the family. Kids loved the pool and game room. We loved the big open living space with kitchen. Would definitely stay again. "
The price is NZ$753
includes taxes & fees
21 Aug - 22 Aug
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

Upscale and Beautiful Beach Front Condo with Gorgeous Gulf Sunsets, South Seas

9.6 out of 10, Exceptional, (87)
"Love how close it was to the water. "
Upscale and Beautiful Beach Front Condo with Gorgeous Gulf Sunsets, South Seas

Captiva Beach Sunset: Gulf Front, Pool, NCIC, 2 Carts, Reserve Fall Dates Now!

9.8 out of 10, Exceptional, (71)
"What a great place and great hosts! First time for our group on North Captiva and it did not disappoint. Tons of wildlife, beautiful property, great fishing and great people. Will be back again!"
Captiva Beach Sunset: Gulf Front, Pool, NCIC, 2 Carts, Reserve Fall Dates Now!

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (90)
"Had an awesome time, perfect place on the beach."
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option

10.0 out of 10, Exceptional, (116)
"We loved north Captiva and the laid back atmosphere. The property was perfect for our large group and the property managers were very helpful."
1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
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