Gasparilla Island Vacation Rentals

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Our top choices for Gasparilla Island vacation rentals

3.0 star property
9.8 out of 10, Exceptional, (1,081 reviews)
"Very nice and relaxing place, staff, very clean room, several amenities, I recommend it."
United States
CARLOS
$236 nightly
The price is $264
Feb 1 - Feb 2
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites

Villa in Matlacha

Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (274 reviews)
"The property was super cute and clean! It also had just about anything you could need!"
United States
Wyatt
$193 nightly
The price is $207
Jan 25 - Jan 26
Total with taxes and fees
Matlacha Tiny Village
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Wonderful setting, terrific host, just right for our one night stay!"
United States
A P.
$105 nightly
The price is $115
Feb 1 - Feb 2
Total with taxes and fees
Tiny home glamping unit in pine island on a 6 acre property
10.0 out of 10, Exceptional, (1 review)
"The remodeling of this older building is amazing! Very comfortable with everything you need. We couldn't get the coffeemaker to work but no problem, we travel with our coffeemaker. Restful and relaxing atmosphere. We would choose this cottage again."
United States
HaroldnMarla J.
$271 nightly
The price is $300
Jan 27 - Jan 28
Total with taxes and fees
Charming 2-bedroom house in Englewood with WiFi and AC

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
$504 nightly
The price is $541
Jan 27 - Jan 28
Total with taxes and fees
Chadwick Cove Resort & Marina
9.8 out of 10, Exceptional, (61 reviews)
"We had a great time even the weather was bad we had an amazing time in the home play games and watch movies "
United States
Adam L.
$289 nightly
The price is $320
Jan 30 - Jan 31
Total with taxes and fees
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
9.2 out of 10, Wonderful, (12 reviews)
"Property was perfect for the price."
United States
William M.
$150 nightly
The price is $167
Jan 25 - Jan 26
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park

Apartment in Olde Englewood Village

Newly renovated only minutes away from the beach!!
9.6 out of 10, Exceptional, (58 reviews)
"Clean, comfortable, everything you need! Owner is great!"
United States
Cheryl L.
$256 nightly
The price is $285
Jan 24 - Jan 25
Total with taxes and fees
Newly renovated only minutes away from the beach!!
9.2 out of 10, Wonderful, (16 reviews)
"Nice location, easy to get into town and access to parks."
United States
Robert B.
$261 nightly
The price is $289
Jan 23 - Jan 24
Total with taxes and fees
Luxury Place - 23017, one block away from Bayshore Park. 3/4 ml of Punta Gorda.

Cottage in Manasota Beach

Cozy Beach Cottage
9.4 out of 10, Exceptional, (24 reviews)
"Wonderful location for a peaceful getaway "
United States
pamela
$430 nightly
The price is $480
Feb 7 - Feb 8
Total with taxes and fees
Cozy Beach Cottage

Vacation Home in Venice East

Venice Dove Shell
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"The host was very welcoming, with timely communication and clear guidelines. The house was spacious, easily accommodating six guests. Also very orderly and clean. I'd recommend this property to friends."
United States
Angela B.
$332 nightly
The price is $370
Jan 26 - Jan 27
Total with taxes and fees
Venice Dove Shell
9.0 out of 10, Wonderful, (11 reviews)
"The location and the property were both ideal for our getaway. "
United States
Trent
$188 nightly
The price is $207
Jan 23 - Jan 24
Total with taxes and fees
Studio#1-Back Bay Sunsets in Matlacha

Residence in Port Charlotte

Port Charlotte Waterfront Home
2.5 star property
$432 nightly
The price is $486
Jan 30 - Jan 31
Total with taxes and fees
Port Charlotte Waterfront Home
2.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"This gem was perfect for my needs. The town doesn't have any chain hotels so my wife suggested I look at Vrbo. This property was just minutes away from where I conducting busy and provided me with my basic needs. Clean, comfy bed, and the property manager was spot on with communications. "
United States
William J. H.
$179 nightly
The price is $198
Jan 26 - Jan 27
Total with taxes and fees
Englewood retreat just 12 minutes from the beach

Apartment in Olde Englewood Village

Paradise in the heart of Old Englewood Village
2.0 star property
$98 nightly
The price is $108
Feb 1 - Feb 2
Total with taxes and fees
Paradise in the heart of Old Englewood Village
9.4 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay at this property! The place was exactly as described — clean, cozy, and well-equipped with everything we needed. The location was perfect, close to everything but still peaceful and relaxing. The host was very responsive and made check-in easy. I would definitely stay here again and recommend it to anyone visiting the area!"
United States
Valerii S.
$330 nightly
The price is $365
Jan 29 - Jan 30
Total with taxes and fees
New Construction with Heated Swim Spa 5,5 mi to the beach with fenced back yard

Villa in Englewood East

Beautiful house with lake view
10.0 out of 10, Exceptional, (10 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
$265 nightly
The price is $293
Jan 25 - Jan 26
Total with taxes and fees
Beautiful house with lake view

Mobile Home in Manasota

The Beach Bus - Skoolie Camping!
9.6 out of 10, Exceptional, (9 reviews)
"A great unique place!"
United States
Jamie L.
$169 nightly
The price is $188
Jan 27 - Jan 28
Total with taxes and fees
The Beach Bus - Skoolie Camping!
9.8 out of 10, Exceptional, (8 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
$135 nightly
The price is $148
Jan 28 - Jan 29
Total with taxes and fees
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
9.6 out of 10, Exceptional, (25 reviews)
"Me and my family really enjoyed our stay at this home and will definitely recommend it to anybody."
United States
Julien L.
$366 nightly
The price is $405
Jan 25 - Jan 26
Total with taxes and fees
Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴
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 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 $207 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.