Gasparilla Island Holiday Rentals

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Our top choices for Gasparilla Island holiday rentals

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is NZ$447
includes taxes & fees
20 May - 21 May
Path to Paradise.

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$420
includes taxes & fees
18 May - 19 May
Charming 2-bedroom house in Englewood with WiFi and AC

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, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is NZ$380
includes taxes & fees
18 May - 19 May
Nestled in North Port. Updated 2 Bed / 1 Bath.

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (287 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is NZ$450
includes taxes & fees
21 May - 22 May
Matlacha Tiny Village

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and nicely decorated condo. Appreciated the extras...dish soap, soap, shampoo and body wash, & TP. Also, beach chairs and towels! Nice outside area and short drive to beaches. Host is very responsive...issue with heat resolved same day. "
United States
Susan E.
The price is NZ$427
includes taxes & fees
18 May - 19 May
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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, (62 reviews)
"Overall was very clean and comfortable, we enjoyed our stay"
United States
Jennifer R.
The price is NZ$421
includes taxes & fees
20 May - 21 May
Completely remodeled beautiful waterfront property on canal with dock

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is NZ$991
includes taxes & fees
18 May - 19 May
Chadwick Cove Resort & Marina

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,204 reviews)
"We had a great stay!!"
United States
Rebecca
The price is NZ$365
includes taxes & fees
9 June - 10 June
The Suites at Fishermen’s Village- 2 Bedroom Suites

Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴

Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴
Port Charlotte
9.4 out of 10, Exceptional, (32 reviews)
"Totally recommend. 5 stars. Very convenient, dozens of stores in 5 minutes."
United States
Yuriy
The price is NZ$684
includes taxes & fees
18 May - 19 May
Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴

Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.4 out of 10, Exceptional, (13 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is NZ$389
includes taxes & fees
18 May - 19 May
Beautiful house with lake view

10 minutes to Mineral Springs w/large Pool and Pet Friendly!

10 minutes to Mineral Springs w/large Pool and Pet Friendly!
North Port
9.6 out of 10, Exceptional, (12 reviews)
"Location was good, beds terrific, inside layout awesome. We had some minor issues which were handled immediately, kudos to management team. "
United States
Gina E.
The price is NZ$626
includes taxes & fees
31 May - 1 June
10 minutes to Mineral Springs w/large Pool and Pet Friendly!

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

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Oakland Hills
9.8 out of 10, Exceptional, (72 reviews)
"Very nice property, close to beaches and shopping. I especially liked that they had pretty much everything you needed for a beach day."
United States
Melissa
The price is NZ$537
includes taxes & fees
21 May - 22 May
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is NZ$690
includes taxes & fees
19 May - 20 May
MALU LANI Inn & Marina

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (24 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is NZ$247
includes taxes & fees
18 May - 19 May
Charming cottage for 2 across warm mineral springs park

Cape Coral Canal Breeze Retreat

Cape Coral Canal Breeze Retreat
Hancock
The price is NZ$1,119
includes taxes & fees
28 May - 29 May
Cape Coral Canal Breeze Retreat

Luxe 3BR Waterfront Stay in Cape Coral

Luxe 3BR Waterfront Stay in Cape Coral
Mariner
10.0 out of 10, Exceptional, (12 reviews)
"Good property for stay witj the family."
United States
Matvei M.
The price is NZ$590
includes taxes & fees
18 May - 19 May
Luxe 3BR Waterfront Stay in Cape Coral

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (52 reviews)
"Apartment was very clean! Lots of outdoor seating options. Nice beach chairs to take to the beach."
United States
Apryl H.
The price is NZ$510
includes taxes & fees
18 May - 19 May
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

The Beach Bus - Skoolie Camping!

The Beach Bus - Skoolie Camping!
Manasota
9.8 out of 10, Exceptional, (13 reviews)
"The schoolie was very comfortably situated as to be off the road and quite private. The hosts were very accommodating and provided the additional needs we requested. It was clean and fully stocked with plenty of bath and beach towels. The outdoor seating area is cute with lots of lush foliage. We enjoyed our stay immensely! "
United States
Michele
The price is NZ$347
includes taxes & fees
18 May - 19 May
The Beach Bus - Skoolie Camping!

New Two story Cozy House Near Warm Mineral Springs

New Two story Cozy House Near Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (23 reviews)
"Host was polite, and responded very quickly . Home was nice . Shared with 2 other workers. When we are back down in that area for work, we will definitely try and book with this host. "
United States
Zachery C.
The price is NZ$782
includes taxes & fees
18 May - 19 May
New Two story Cozy House Near Warm Mineral Springs

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"Couldn’t been better"
United States
Louis
The price is NZ$530
includes taxes & fees
18 May - 19 May
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
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$365 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.