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
9.8 out of 10, Exceptional, (564)
"I wish there was a gym and decent pool. It would also be great to offer more breakfast options."
The price is NZ$325
includes taxes & fees
19 Jun - 20 Jun
The Suites at Fishermen’s Village- 2 Bedroom Suites
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (232)
"Great lil place, loved it!! "
The price is NZ$370
includes taxes & fees
17 Jun - 18 Jun
Matlacha Tiny Village
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
9.4 out of 10, Exceptional, (85)
"Walked on beach and collected shells. It was very nice and relaxing. Had the best sleep her than I have had in a long time. Nice people ont he island"
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
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Privacy in Paradise
10.0 out of 10, Exceptional, (58)
"Heat place to stay and anchor our adventures from. Thank you!"
Privacy in Paradise
NEW LISTING! Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning
8.0 out of 10, Very good, (2)
"While many homes in this neighborhood are still struggling to recover from hurricane Ian, this cozy litte place is primed for the tourist season! Recently updated with very pretty, Florida decor, and sitting right on the canal for easy access to the gulf, our time spent here was relaxing and pleasant indeed. One thing to note is, it may not be a good fit for an older person who is prone to falls. I care for my mom, and would not have wanted to bring her here, as most of the rooms are on...
NEW LISTING! Flamingo Bay Cottage (3-Bedroom) with Pool - Pets Allowed by RedAwning
Waterfront Villa with unique view of wide canal and nature preserve - Pool & Spa
9.8 out of 10, Exceptional, (156)
"We absolutely loved everything about Villa Amara. Our hosts were incredibly kind and communicative and super helpful with all our questions. The villa is in a wonderful location in Cape Coral, and the house and the entire property is so well-kept, lovely, and homey. The view from the lanai and pool is stunning; we spent hours just sitting on the porch watching the water, trees, and birds. The house is beautifully appointed with everything guests could need for a comfortable stay. My husband and...
Waterfront Villa with unique view of wide canal and nature preserve - Pool & Spa
3/2 home on Little Gasparilla Island - Gulf of Mexico. Private beach and dock!
10.0 out of 10, Exceptional, (29)
"The home was exactly as advertised. It was well stocked, clean and very peaceful. It was close to the beach and close to the dock for our boat. Communication with the owners was great and their home exceeded our expectations. We look forward to visiting again and highly recommend this property."
3/2 home on Little Gasparilla Island - Gulf of Mexico. Private beach and dock!
🔆🏝LITTLE PARADISE🏝🔆
10.0 out of 10, Exceptional, (29)
"Nice place very comfortable. Enjoyed pool and golf cart."
🔆🏝LITTLE PARADISE🏝🔆
Steps From Beach. Private entrance.
9.8 out of 10, Exceptional, (73)
"We had a great time, place was nice, so close to the beach, provided everything we needed for spending a weekend at the beach. We will definitely be back! Thanks so much for letting us stay at your place!"
Steps From Beach. Private entrance.
Quiet Lemon Bay with Pool, Beach and Pier
9.8 out of 10, Exceptional, (25)
"The property and host are both VERY NICE! The location is Excellent! You can walk right from your porch to a dock on Lemon Bay with wonderful views, and you're just a few minutes drive to the beach."
Quiet Lemon Bay with Pool, Beach and Pier
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
9.8 out of 10, Exceptional, (37)
"We had an amazing time the house provided everything we were looking for. The pool and hot tub is where we spent our time. The location was close to everything we needed."
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!
The Turtle House-Miles and Miles of Private Beach-Sunset Views
9.4 out of 10, Exceptional, (13)
"What a great experience and beautiful location! We are from Miami and we never get tired of great finds like this one. Andrew was really nice and attentive, and extremely accommodating. We were right on the beach! Exclusivity is a guarantee. Will definitely be returning again!"
The price is NZ$2,189
includes taxes & fees
21 Jun - 22 Jun
The Turtle House-Miles and Miles of Private Beach-Sunset Views
2-Bedroom Pool Home Convenient To Beaches
9.8 out of 10, Exceptional, (111)
"Extremely clean!!! The pool area is private with a wooded area directly behind the house. Highly recommend!!!"
2-Bedroom Pool Home Convenient To Beaches
Charmingly colorful home with deck, beach gear, AC & W/D - dog-friendly
9.4 out of 10, Exceptional, (3)
"Location is marvelous: Quiet, surrounded by nature. The porch alone is worth the stay, and having the beach a mere mile or so down the road? Eliminates questions about what to do (but bring footware!) Challenges: keycode system is insane, and also non-functional. Glad we had the keys instead. Especially as the promised beach towels were still in the cellar. Thanks to Vacasa team for working us through the entry issues. Otherwise? Spectacular location, very comfortable, and surrounded by all...
Charmingly colorful home with deck, beach gear, AC & W/D - dog-friendly
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
10.0 out of 10, Exceptional, (31)
"This rental was very dreamy. It was clean, affordable, easy to talk to the landlord, and had many ammenities. They had some beach equiptment for when we went to the beach as well as beach towels. The neighborhood was great and we felt like we could come and go as needed. We would absolutely stay here again. Thank you!"
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
Charming studio, fully renovated in 2024. Minutes from the beach & pet friendly.
10.0 out of 10, Exceptional, (5)
"I was in town for work and this studio was in the absolute best location for me. 20 minutes from work and family and only few minutes to downtown Venice. The studio was in a perfect location. It's in a very quaint little neighborhood. It was very clean and the property taken care of. Laurie reached out a few times to make sure my stay was going well. She was very attentive to her guest. I will 100% be booking here agian for my trips."
The price is NZ$213
includes taxes & fees
22 Jun - 23 Jun
Charming studio, fully renovated in 2024. Minutes from the beach & pet friendly.
Palm Island beach home with private pool. Island PARADISE awaits!!!
10.0 out of 10, Exceptional, (112)
"The island is stunning!! Beach was very quiet, the restaurant on the island was great. We had such a nice stay. The house was spotless, and we had just about every thing we needed. The pool was super clean, and perfect to use after trips to the beach. Thanks again!"
Palm Island beach home with private pool. Island PARADISE awaits!!!
NEW! Waterfront Pool Home Canal Front in Quiet Area
9.2 out of 10, Wonderful, (10)
"Nice clean place that’d be great for a family. Pool was fantastic. Plenty of food options in a 10 minute or so radius. Would stay again."
NEW! Waterfront Pool Home Canal Front in Quiet Area
Newly built. Heated pool. Ideal for poolside relaxing and romantic gateways
9.8 out of 10, Exceptional, (20)
"New to VRBO. Loved this house, decor, pool, and hosts. Comfortable King bed, great pressure and hot water in the showers, pool and lanai made the difference. The first day was chilly but the heated pool allowed us to not miss a pool day. Highly recommend this house and hosts."
Newly built. Heated pool. Ideal for poolside relaxing and romantic gateways
Perfect getaway! Newly remodeled waterfront suite.
8.6 out of 10, Excellent, (22)
"This place was absolutely perfect for my mother and I. The location was easily accessed. The hosts are so kind and as a bonus, they have a sweet little cat who loves to welcome their guests. I'd 100% recommend and would stay again."
Perfect getaway! Newly remodeled waterfront suite.
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See all available properties in Gasparilla Island
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.

Other types of properties in Gasparilla Island you may be interested in

Boca Grande Hotel
2.5 star property
8.6 out of 10, Excellent, (472)
"More like a motel,than hotel, but it was good, quiet, clean "
The price is NZ$298
includes taxes & fees
9 Jun - 10 Jun
Boca Grande Hotel
Sunseeker Resort Charlotte Harbor
4.0 star property
9.2 out of 10, Wonderful, (288)
"It was very neat clean well cared for"
The price is NZ$346
includes taxes & fees
26 Jun - 27 Jun
Sunseeker Resort Charlotte Harbor
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (564)
"I wish there was a gym and decent pool. It would also be great to offer more breakfast options."
The price is NZ$325
includes taxes & fees
19 Jun - 20 Jun
The Suites at Fishermen’s Village- 2 Bedroom Suites
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gasparilla Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gasparilla Island. 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 Gasparilla Island. 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 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 holiday 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 Gasparilla Island short-term rentals, that won’t be hard to do.

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