Gasparilla Island Holiday Rentals

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Our top choices for Gasparilla Island holiday rentals

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 AU$331
includes taxes & fees
26 Apr - 27 Apr
Charming 2-bedroom house in Englewood with WiFi and AC

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 AU$348
includes taxes & fees
27 Apr - 28 Apr
Completely remodeled beautiful waterfront property on canal with dock

Coastal Quadruplex with private beach access & deck - dog-friendly

Coastal Quadruplex with private beach access & deck - dog-friendly
Manasota Key
8.4 out of 10, Very good, (20 reviews)
"We enjoyed the place even though we slept and showered there . Quiet. Clean "
United States
Dollie
The price is AU$535
includes taxes & fees
27 Apr - 28 Apr
Coastal Quadruplex with private beach access & deck - dog-friendly

Dog-Friendly Quadruplex w/Snowbird Discounts and Private Beach Access

Dog-Friendly Quadruplex w/Snowbird Discounts and Private Beach Access
Manasota Key
9.0 out of 10, Wonderful, (12 reviews)
"Perfect getaway beach trip."
United States
jill s.
The price is AU$535
includes taxes & fees
27 Apr - 28 Apr
Dog-Friendly Quadruplex w/Snowbird Discounts and Private Beach Access

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, (68 reviews)
"Had a great stay. Host was responsive and the home was very clean. Great location in a quiet residential area, but close enough to get to all activities in a short drive. Many grocery stores around too. We are pleased with our choice. "
United States
Delanie M.
The price is AU$447
includes taxes & fees
30 Apr - 1 May
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (286 reviews)
"Super cute place!! Super clean and comfortable."
United States
Francesca
The price is AU$388
includes taxes & fees
26 Apr - 27 Apr
Matlacha Tiny Village

Tiny home glamping unit in pine island on a 6 acre property

Tiny home glamping unit in pine island on a 6 acre property
Saint James City
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
The price is AU$193
includes taxes & fees
29 Apr - 30 Apr
Tiny home glamping unit in pine island on a 6 acre property

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (37 reviews)
"Me and my significant other took a little mini vacation wonderful house. It was very clean very beautiful inside, I like the beach vibes beautiful bedrooms. I recommend anybody to book this place. If I had to go back, I’ll book again. "
United States
Alexus
The price is AU$465
includes taxes & fees
26 Apr - 27 Apr
Mimosa Memories

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is AU$430
includes taxes & fees
26 Apr - 27 Apr
Path to Paradise.

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, (22 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is AU$311
includes taxes & fees
26 Apr - 27 Apr
Nestled in North Port. Updated 2 Bed / 1 Bath.

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is AU$811
includes taxes & fees
25 Apr - 26 Apr
Chadwick Cove Resort & Marina

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, (17 reviews)
"Couldn’t been better"
United States
Louis
The price is AU$432
includes taxes & fees
7 May - 8 May
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

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, (22 reviews)
"Mike was a great host. Was very responsive to any questions. The property is exceptional. It was everything we needed."
United States
Barbara E.
The price is AU$453
includes taxes & fees
2 May - 3 May
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

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 AU$422
includes taxes & fees
3 May - 4 May
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Great Escape Luxe Retreat

Great Escape Luxe Retreat
Pelican
9.4 out of 10, Exceptional, (8 reviews)
"We had a fantastic weekend stay! The home was incredibly comfortable and had everything we needed. The highlight was definitely the pool—perfect for relaxing and spending quality time together. We truly enjoyed our stay and would love to come back!"
United States
Omar D.
The price is AU$521
includes taxes & fees
30 Apr - 1 May
Great Escape Luxe Retreat

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, (10 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 AU$518
includes taxes & fees
27 Apr - 28 Apr
10 minutes to Mineral Springs w/large Pool and Pet Friendly!

Home in quiet Bird Sanctuary Neighborhood, close to Beach

Home in quiet Bird Sanctuary Neighborhood, close to Beach
South Venice
9.6 out of 10, Exceptional, (19 reviews)
"Good location for us"
United States
EdgefieldFarm
The price is AU$483
includes taxes & fees
25 Apr - 26 Apr
Home in quiet Bird Sanctuary Neighborhood, close to Beach

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (22 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is AU$212
includes taxes & fees
2 May - 3 May
Charming cottage for 2 across warm mineral springs park

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 AU$483
includes taxes & fees
7 May - 8 May
Luxe 3BR Waterfront Stay in Cape Coral

Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds

Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds
South Venice
10.0 out of 10, Exceptional, (40 reviews)
"The hosts Dorcia and Mac provide a quality vacation rental that feels like home. We enjoyed the pool and comfortable home. Any questions were quickly answered. The home has everything you could need during your vacation."
United States
R P.
The price is AU$649
includes taxes & fees
5 May - 6 May
Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds
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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Top Gasparilla Island Hotel Reviews

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 favourite 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 depend 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 AU$370 per night. Entering your travel dates in the search wizard might find you 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.