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

This weekend
Next weekend

Holiday Rentals in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (948)
"Great stay"
The price is NZ$317
includes taxes & fees
30 July - 31 July
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 **

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (259)
"Amazing little place. Not so little. Lovely. Excellent host and proximity to everything! "
The price is NZ$307
includes taxes & fees
6 Aug - 7 Aug
Matlacha Tiny Village

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

10.0 out of 10, Exceptional, (4)
"We had been looking forward to our family vacation for quite awhile with excitement and the home did not disappoint! Clean, light and bright with a stunning view. We will definitely be back!"
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (8)
"Wonderful place to stay, quiet, close to the beach and wonderful restaurants within walking distance! Highly recommend!!!"
The price is NZ$897
includes taxes & fees
19 Aug - 20 Aug
Chadwick Cove Resort & Marina

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

10.0 out of 10, Exceptional, (20)
"This property is the best appointed rental we have stayed at in Cape Coral. Has everything you will need for your stay. Great location, great pool. Lived it. "
Luxury GULF access! DOCK/SPA/Pool/GAME ROOM

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

9.4 out of 10, Exceptional, (45)
"This is a cute, clean, comfortable property. The host was super helpful and friendly. We loved it and will definitely be coming back."
The price is NZ$257
includes taxes & fees
27 July - 28 July
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (77)
"The property was outstanding. The owners were marvelous would definitely go back."
Paradise Cove at Lemon Bay

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

9.2 out of 10, Wonderful, (55)
"Loved our stay! "
The price is NZ$584
includes taxes & fees
2 Aug - 3 Aug
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

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

9.0 out of 10, Wonderful, (16)
"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

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

9.8 out of 10, Exceptional, (106)
"Owners & property managers were amazing & responsive. Beautiful home & location "
New luxury pool home, 2 min to beach, 360 water views, club available

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

8.0 out of 10, Very good, (17)
"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$761
includes taxes & fees
13 Aug - 14 Aug
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

🔆🏝LITTLE PARADISE🏝🔆

10.0 out of 10, Exceptional, (35)
"Loved the property! They thought of everything! So comfortable and inviting! "
🔆🏝LITTLE PARADISE🏝🔆

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!

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

9.6 out of 10, Exceptional, (83)
"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, (68)
"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!

Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!

9.2 out of 10, Wonderful, (15)
"The space was as advertised, clean and just the right size for us. Despite colder than normal temperatures, we had a great getaway and really enjoyed the hot tub."
The price is NZ$411
includes taxes & fees
6 Aug - 7 Aug
Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.6 out of 10, Excellent, (12)
"Overall nice property. Bed was comfortable and location was nice. We enjoyed the pool and hot tub. Walking distance to beach. Our TV didn’t work upon arrival, and they quickly fixed it, very courteous. "
South Seas Bayside Villa 5130: Your Perfect Island Retreat

Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.

9.2 out of 10, Wonderful, (45)
"Enjoyed our stay. Very nice hosts."
Fish, Swim, Boat, Kayak, Snorkel, Bike, Hike, Dolphin Watch and Island Hopping.

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

9.8 out of 10, Exceptional, (177)
"House was nice and had great location!"
The price is NZ$732
includes taxes & fees
5 Aug - 6 Aug
120 steps to beach! Safely on the beach side of the road!
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