Vacation Rentals in Gasparilla Island

Start comparing over 78 rentals in Gasparilla Island and book at the best price!

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Vacation housesVillasAir conditioningPrivate pool

8.0

Vacation Rentals in Gasparilla Island

Vacation rental for 2 people, with pool and hot tub as well as balcony

1 bedroom

9.8

(28 reviews)

from $273 / nightFREE cancellation

Vacation rental for 2 people

1 bedroom

10.0

(2 reviews)

from $149 / nightFREE cancellation

Hotel for 3 people, with pool

1 bedroom

9.6

(9 reviews)

from $188 / nightFREE cancellation

Vacation rental for 4 people, with hot tub and pool as well as yard

1 bedroom

9.6

(32 reviews)

from $379 / nightFREE cancellation

Vacation rentals with free cancellation

Vacation rental for 4 people, with yard

2 bedrooms

9.8

(33 reviews)

from $322 / nightFREE cancellation

Hotel for 3 people, with pool

1 bedroom

10.0

from $168 / nightFREE cancellation

Vacation rental for 2 people, with yard

1 bedroom

9.8

(55 reviews)

from $473 / nightFREE cancellation

Vacation rental for 4 people, with balcony

2 bedrooms

10.0

(21 reviews)

from $903 / nightFREE cancellation

Vacation rentals in city center

Vacation rental for 4 people, with balcony and pool

2 bedrooms

10.0

from $447 / nightFREE cancellation

Vacation rental for 2 people

1 bedroom

10.0

(3 reviews)

from $222 / nightFREE cancellation

Vacation rental for 4 people, with yard

2 bedrooms

9.9

(48 reviews)

from $653 / nightFREE cancellation

Vacation rental for 4 people

2 bedrooms

10.0

from $369 / night

Vacation rentals with pets allowed

Pets allowed

Vacation rental for 8 people, with yard and balcony

4 bedrooms

10.0

(27 reviews)

from $554 / nightFREE cancellation

Pets allowed

Vacation rental for 6 people, with pets

3 bedrooms

9.8

(48 reviews)

from $754 / nightFREE cancellation

Pets allowed

Vacation rental for 10 people, with balcony and hot tub

5 bedrooms

9.9

(40 reviews)

from $2,046 / night

Pets allowed

Vacation rental for 8 people, with balcony and yard

4 bedrooms

from $712 / night

Vacation Rentals with Pool

Pool

Hotel for 5 people, with pool

1 bedroom

8.0

(5 reviews)

from $177 / night

Pool

Vacation rental for 6 people, with pool and balcony as well as hot tub

2 bedrooms

8.0

from $360 / nightFREE cancellation

Pool

Vacation rental for 6 people, with pool and hot tub as well as yard

2 bedrooms

9.9

(23 reviews)

from $503 / nightFREE cancellation

Pool

Hotel for 5 people, with pool

1 bedroom

7.3

(3 reviews)

from $168 / nightFREE cancellation

Find Vacation Rentals in Gasparilla Island

Best Vacation Rentals in Gasparilla Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Vacation Rental for 2 Guests in Boca Grande, Gasparilla Island

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Boca Grande, Gasparilla Island

Vacation Rental • 592 ft² • 1 Bedroom

Boca Grande, Gasparilla Island

9.8

(55 reviews)

This Spanish style guest house is exceedingly private and offers one of the best locations on the island. A mere 100 yards from beautiful Gulf of Mexico beach and a short 3 block walk into town where one can find wonderful shopping, as well as fabulous restaurants and a bakery. One bedroom with queen bed; modern bath with large shower, large sitting room with flat screen TV and WiFi. Kitchenette with two burner cooktop, small sink, mini fridge, microwave, and coffee maker. Guest house has terra cotta tile floors and historical ceiling beams. Located on larger property with lawns and beautif...

from $473 / night

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Vacation Rental for 6 Guests in Gasparilla Island, Charlotte County

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Gasparilla Island, Charlotte County

Vacation Rental • 1345 ft² • 2 Bedrooms

Gasparilla Island, Charlotte County

9.9

(23 reviews)

This completely updated 2nd floor condo is as close as you can get to the ocean. Just steps from the water at high tide. The 2 bedroom, 2 full bath unit sleeps 6, has an updated kitchen w quartz counter tops and is tastefully, and professionally decorated throughout. The living room and dining room overlooks the ocean with new furnishings in 2020. The master features a king with bath w walk in shower and large closet, the 2nd BR has 2 doubles w full bath. Watch the sunset from the screened patio with seating for 4 or the open balcony seating for 2. A fully stocked kitchen, unit specific sec...

from $503 / night

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Vacation Rental for 4 Guests in Boca Grande, Gasparilla Island

Vacation Rental for 4 Guests in Boca Grande, Gasparilla Island, Picture 1

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Boca Grande, Gasparilla Island

Vacation Rental • 4 Guests • 2 Bedrooms

Boca Grande, Gasparilla Island

9.9

(48 reviews)

PLEASE NOTE: We rent by the week-Saturday to Saturday- December 1 thru April 30. During the rest of the year we have a strict 4 night minimum.PLEASE NOTE: While a well behaved dog is welcome, we have had to institute a strict ONE DOG policyPLEASE NOTE: We do not discount our rates.Enjoy the most relaxing vacation week of your life. Park your car and walk, bike, or golf cart everywhere on island! This charming, refurbished, 2 bedroom, 2 bath cottage with courtyard entrance is located in the Historic District within easy walking distance to town and beach. It offers an open floor plan with 2,...

from $653 / night

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Popular Destinations in Gasparilla Island

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Prices and availability

Current Vacation rental prices Gasparilla Island

$469for 27 Apr - 4 May

$576 annual average

May

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Aug

Oct

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Dec

Jan

Average price per week

Current vacation rental availability Gasparilla Island

15%for 27 Apr - 4 May

47% annual average

May

Jun

Jul

Aug

Oct

Nov

Dec

Jan

Percentage of available rentals

FAQs: Vacation Rentals in Gasparilla Island

On average, what was the cost for vacation rentals on Gasparilla Island last year?

Last year, rentals in Gasparilla Island had an annual average price of around $522 per night.

During which months are vacation rentals cheaper on Gasparilla Island?

If you want to save as much as possible during your vacation to Gasparilla Island, go there in August ($477 per night on average), September ($490), or October ($499), to find the lowest prices for the whole year.

When are vacation rentals more expensive on Gasparilla Island?

Last year, the month that had the highest annual average on Gasparilla Island was February, with an average price of $598 per night. This was followed by December, with an average of $593, and then March, with $533.

Are there usually many vacation rentals available on Gasparilla Island?

It is better to book sooner than later on Gasparilla Island as only 20% of the accommodations remain available throughout the year, according to last year's data.

What time of the year can I find more available vacation rentals?

Last year, the months with the largest number of properties available of the year on Gasparilla Island were September, August and October, with average availabilities of 56%, 52%, and 45%, respectively.

How many rentals are there on Gasparilla Island?

Our inventory features approximately 100 vacation rentals from 3 partners, giving you plenty of choices when searching for your next dream vacation rental!