Gasparilla Island Vacation Rentals

Vacation Rentals in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (564)
"All Staff was professional and friendly ... even received some information on fishing spots from frint desk ( thank you young lady lol ) will definitely ma k e a return trip "
The price is $199
$223 total
includes taxes & fees
Jun 9 - Jun 10
The Suites at Fishermen’s Village- 2 Bedroom Suites
Matlacha Tiny Village
Dock
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (232)
"We had a very nice stay at the tiny house! (Keep in mind, it is tiny) But very comfortable!! An unique experience and the property was outstanding compared to all the other units in the vicinity. It had a nice spacious canal front deck, and kayaks with a launching deck. Complete mini kitchen and great coffee preps. The beds were very comfortable and unit was very clean and updated. Decorated nicely! Loved the loft! Great alternative to a hotel room. We would definitely stay at Matlacha Tiny...
The price is $138
$229 total
includes taxes & fees
Jun 9 - Jun 10
Matlacha Tiny Village
Amazing location! Beachfront Island Cottage On The Gulf "Old" FL still exists!!
Beach | On the beach
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!!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Privacy in Paradise
Beach
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
Fridge, microwave, oven, coffee/tea maker
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
Pool | Outdoor pool, a heated pool
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!
On the beach, sun loungers, beach towels
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🏝🔆
Fridge, microwave, oven, stovetop
🔆🏝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.
Beach nearby, sun loungers, beach towels
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
Property grounds
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!
Outdoor pool, a heated pool
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
Outdoor dining
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 $788
$1,352 total
includes taxes & fees
Jun 21 - Jun 22
The Turtle House-Miles and Miles of Private Beach-Sunset Views
2-Bedroom Pool Home Convenient To Beaches
Pool
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
TV, fireplace
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
Beach
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.
Terrace/patio
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 $79
$132 total
includes taxes & fees
Jun 8 - Jun 9
Charming studio, fully renovated in 2024. Minutes from the beach & pet friendly.
Palm Island beach home with private pool. Island PARADISE awaits!!!
Exterior
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
Outdoor dining
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
Fridge, microwave, oven, stovetop
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.
Property grounds
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.
Don't see what you're looking for?
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.

Gasparilla Island Vacation Rental Travel Info

Popular accommodation
Gasparilla Island private vacation homes
International airports
Fort Myers, FL (RSW-Southwest Florida Intl.) and Punta Gorda, FL (PGD-Charlotte County)

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

Boca Grande Hotel
Room, 1 King Bed | Down comforters, iron/ironing board, free WiFi, bed sheets
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 $165
$184 total
includes taxes & fees
Jun 9 - Jun 10
Boca Grande Hotel
Sunseeker Resort Charlotte Harbor
2 outdoor pools, open 8:00 AM to 8:30 PM, cabanas (surcharge)
Sunseeker Resort Charlotte Harbor
4.0 star property
9.2 out of 10, Wonderful, (288)
"Great property and beautiful room"
The price is $161
$214 total
includes taxes & fees
Jun 26 - Jun 27
Sunseeker Resort Charlotte Harbor
The Suites at Fishermen’s Village- 2 Bedroom Suites
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (564)
"All Staff was professional and friendly ... even received some information on fishing spots from frint desk ( thank you young lady lol ) will definitely ma k e a return trip "
The price is $199
$223 total
includes taxes & fees
Jun 9 - Jun 10
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.

Everything you need to know about Gasparilla Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gasparilla Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gasparilla Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Gasparilla Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gasparilla Island rentals

At Expedia, we put the best Gasparilla Island vacation 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 vacation.

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.

Recent reviews of Gasparilla Island properties
Expedia verified reviews

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

5/5 Excellent
"All Staff was professional and friendly ... even received some information on fishing spots from frint desk ( thank you young lady lol ) will definitely ma k e a return trip "
A verified traveler stayed at The Suites at Fishermen’s Village- 2 Bedroom Suites
Posted 3 days ago
The Suites at Fishermen’s Village- 2 Bedroom Suites