Gasparilla Island Holiday Rentals

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Holiday Rentals in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1031)
"We loved our stay and plan on returning. Loved the sunset cruise from the marina "
United States
Paul
The price is NZ$410
includes taxes & fees
18 Nov - 19 Nov
The Suites at Fishermen’s Village- 2 Bedroom Suites

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

North Captiva
9.6 out of 10, Exceptional, (100)
"Everything was perfect."
United States
Tom C.
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

4 Bedroom Beach Home on a Private Island with a Private Pool

North Captiva
9.8 out of 10, Exceptional, (26)
"My family and I (8 adults) stayed at Sandy Feet during the week of New Years, and had a great time. The home is absolutely gorgeous, and accurately described in the listing. We all had fun using the pool and foosball tables, laying out on the deck(s), of course walking the beach. This home has everything you could possibly want to make your vacation on North Captiva a success. Yamirka (owner) and Tortuga Properties were both very communicative and responsive to whatever questions we had. ...
United States
Daniel W.
4 Bedroom Beach Home on a Private Island with a Private Pool

Matlacha Tiny Village

3.0 star property
Matlacha
8.8 out of 10, Excellent, (266)
"Amazing spot. Love it. Quiet, and very suitable for us. The hosts are amazing; they will do anything in their power to accommodate your needs. Highly recommend it."
United States
Isabel
The price is NZ$360
includes taxes & fees
19 Nov - 20 Nov
Matlacha Tiny Village

2 Private Cabanas with kitchen and a Private Pool.

Pelican
9.4 out of 10, Exceptional, (26)
"Property manager was great. Really enjoyed our stay. Would highly recommend others to stay here. "
United States
David H.
2 Private Cabanas with kitchen and a Private Pool.

Chadwick Cove Resort & Marina

4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"I don't care about tiki bars and pools, so this was great for me. beach access is a short walk, the unit was modern and clean. "
United States
Billie
The price is NZ$942
includes taxes & fees
18 Nov - 19 Nov
Chadwick Cove Resort & Marina

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

Trafalgar
10.0 out of 10, Exceptional, (42)
"Very beautiful home with a great pool. We throughly enjoyed our stay and the management was very accommodating during our stay. The bikes, beach toys and coolers were great to have during our stay."
United States
Lesley B.
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

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

North Captiva
9.2 out of 10, Wonderful, (19)
"The property and entire process was great. The owner and hosts had great communication from booking to check out. The house was well stocked with everything needed from kitchen supplies to games to play. Great having the pool area to cook dinner while my daughters were playing. We would definitely book here again."
United States
Kevin S.
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

3.0 star property
Pelican
10.0 out of 10, Exceptional, (22)
"This home was a great property. Plenty of kitchen tools. The pool and patio right on the canal were special. From the bikes, kayaks and outdoor bbq, to the 2 master suites, this place had everything. There was a park a mile away with basketball, pickleball, tennis as well. Would definitely stay here again!"
United States
Lance H.
NEW EVERYTHING!! 4-bed 3 bath South Facing spill over spa pool. 2 king suites

Paradise Cove at Lemon Bay

3.5 star property
Olde Englewood Village
8.2 out of 10, Very good, (79)
"Nice property and very inviting. I especially liked the dock."
United States
David
Paradise Cove at Lemon Bay

Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views

North Captiva
9.8 out of 10, Exceptional, (72)
"Great trip!"
United States
Patricia D.
Big on the Beach House 6BR Home + Club Access, Private Dock & Stunning Views

South Seas Bayside Villa 5130: Your Perfect Island Retreat

Captiva
8.4 out of 10, Very good, (19)
"Beautiful apartment "
United States
Michael
South Seas Bayside Villa 5130: Your Perfect Island Retreat

BEACHFRONT LUXURY ISLAND HOME PRIVATE SWIM SPA~DOCK FISHING~GOLF CART STUNNING

North Captiva
10.0 out of 10, Exceptional, (5)
"We loved the outdoor patio and view! Excellent outdoor furniture! "
United States
dana t.
BEACHFRONT LUXURY ISLAND HOME PRIVATE SWIM SPA~DOCK FISHING~GOLF CART STUNNING

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

Trafalgar
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 NZ$1,608
includes taxes & fees
18 Nov - 19 Nov
Pet friendly spacious home for large groups! Heated pool & jacuzzi, games!

Private Elevated Pool & Deck!

North Captiva
9.4 out of 10, Exceptional, (45)
"Fantastic home and wonderful stay. Any inquires we had were addressed pleasantly and quickly. The home is very clean and well stocked with everything we needed to cook or grill. Beds were comfortable. We enjoyed the deck pool daily. I plan on staying here again in the future. Highly recommend."
United States
Karen H.
Private Elevated Pool & Deck!

Schell-Topia: Lake Front

Hancock
10.0 out of 10, Exceptional, (168)
"We had an exceptional experience. Everything we needed and then some. Would visit again. "
United States
Anonymous traveller
Schell-Topia: Lake Front

Pool Side Paradise in Southwest Cape Coral NO CHARGE HEATED POOL fenced yard

Pelican
9.8 out of 10, Exceptional, (105)
"Very accommodating and sweet"
United States
Macey A.
Pool Side Paradise in Southwest Cape Coral NO CHARGE HEATED POOL fenced yard

BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL

North Captiva
10.0 out of 10, Exceptional, (11)
"Multigenerational vacation was amazing ! They have done amazing work to get the island back up and ready for vacationers after Hurricane Ian. We hope to come again!"
United States
Julie S.
BEAUTY AND THE BEACH- BEACHFRONT MANSION, HEATED POOL

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

Captiva
9.6 out of 10, Exceptional, (90)
"The place was great - I would be helpful to know what is already there so the renters did not have to buy/rent additional items (ex: beach chairs& umbrella) "
United States
Eric R.
Upscale and Beautiful Beach Front Condo with Gorgeous Gulf Sunsets, South Seas

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

North Captiva
9.8 out of 10, Exceptional, (110)
"We had a wonderful time staying here. Everything was easy and relaxed. An amazing view from the lookout deck and easy walk or golf cart ride to the beach. "
United States
Page M.
New luxury pool home, 2 min to beach, 360 water views, club available
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.
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Find out more about Gasparilla Island

Everything you need to know about Gasparilla Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gasparilla Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gasparilla Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gasparilla Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gasparilla Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gasparilla Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gasparilla Island holiday rentals we have selected for you start as low as NZ$360 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gasparilla Island rentals

At Expedia, we put the best Gasparilla Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gasparilla Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gasparilla Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gasparilla Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.