Gasparilla Island Vacation Rentals

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Our top choices for Gasparilla Island vacation rentals

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 CA $98
CA $335 total
includes taxes & fees
May 5 - May 6
Completely remodeled beautiful waterfront property on canal with dock

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 CA $145
CA $440 total
includes taxes & fees
May 3 - May 4
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

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 CA $139
CA $182 total
includes taxes & fees
Apr 30 - May 1
Tiny home glamping unit in pine island on a 6 acre property

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 CA $203
CA $431 total
includes taxes & fees
May 4 - May 5
Matlacha Tiny Village

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, (23 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is CA $117
CA $301 total
includes taxes & fees
May 3 - May 4
Nestled in North Port. Updated 2 Bed / 1 Bath.

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 CA $153
CA $471 total
includes taxes & fees
Apr 30 - May 1
Home in quiet Bird Sanctuary Neighborhood, close to Beach

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 CA $92
CA $319 total
includes taxes & fees
May 27 - May 28
Charming 2-bedroom house in Englewood with WiFi and AC

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 CA $156
CA $788 total
includes taxes & fees
Apr 29 - Apr 30
Chadwick Cove Resort & Marina

Sunshine Hideaway 6 mins to Warm Mineral Springs

Sunshine Hideaway 6 mins to Warm Mineral Springs
North Port
10.0 out of 10, Exceptional, (8 reviews)
"Home was clean and inviting, and served us well during our stay. Loved the Christmas decorations! "
United States
Andrea and Dennis B.
The price is CA $143
CA $355 total
includes taxes & fees
Apr 29 - Apr 30
Sunshine Hideaway 6 mins to Warm Mineral Springs

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 CA $75
CA $204 total
includes taxes & fees
May 17 - May 18
Charming cottage for 2 across warm mineral springs park

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, (22 reviews)
"Had an awesome with friends and family and will stay again if we’re in the area."
United States
Eric H.
The price is CA $153
CA $626 total
includes taxes & fees
Apr 29 - Apr 30
New Two story Cozy House Near Warm Mineral Springs

Myakka River

Myakka River
Venice
10.0 out of 10, Exceptional, (21 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is CA $252
CA $631 total
includes taxes & fees
Apr 29 - Apr 30
Myakka River

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is CA $146
CA $419 total
includes taxes & fees
Apr 29 - Apr 30
Path to Paradise.

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 CA $204
CA $427 total
includes taxes & fees
Apr 30 - May 1
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

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 CA $280
CA $557 total
includes taxes & fees
Apr 29 - Apr 30
MALU LANI Inn & Marina

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 CA $129
CA $507 total
includes taxes & fees
May 11 - May 12
10 minutes to Mineral Springs w/large Pool and Pet Friendly!

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 CA $251
CA $640 total
includes taxes & fees
May 4 - May 5
Relaxing Poolside- a Private Oasis -heated pool- 7min to beach-2 King beds

Beautiful house with lake view

Beautiful house with lake view
Englewood East
10.0 out of 10, Exceptional, (11 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is CA $183
CA $297 total
includes taxes & fees
May 3 - May 4
Beautiful house with lake view
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gasparilla Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.