Gasparilla Island Vacation Rentals

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Vacation Rentals in Gasparilla Island

Our top choices for Gasparilla Island vacation rentals

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (966)
"Great stay"
The price is CA $214
CA $240 total
includes taxes & fees
Aug 28 - Aug 29
The Suites at Fishermen’s Village- 2 Bedroom Suites

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

9.6 out of 10, Exceptional, (97)
"Everything was perfect."
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (263)
"Very nice place with all necesary accommodations for a Pleasant stay. "
The price is CA $136
CA $255 total
includes taxes & fees
Aug 26 - Aug 27
Matlacha Tiny Village

“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

10.0 out of 10, Exceptional, (5)
"This property is amazing! Beautiful views and great fishing right off the dock. My wife and I stayed for our belated anniversary and we couldnt have been happier. We will be back."
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING

PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

10.0 out of 10, Exceptional, (41)
"We had a wonderful time!"
PALM BREEZE - SWIM UP TO THE BAR! Integrated spa, Outdoor grill, Fire pit!

Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

9.0 out of 10, Wonderful, (18)
"We took our multigenerational family for a few days of quiet & sunshine. They loved the place so mush that they want to go back next year!We had a few problems with the house but the management team made it right.Lovely place to spend a few days - or more!"
Fully renovated Luxury House pool! HUGE 5 BD 5 BA 9 bed! Sleeps 16! 2 golf carts

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"We enjoyed our stay so much! Just right for us with short walks to the Beach and Bay, peaceful back porch and comfy beds. It is a beautiful and clean house in the trees. Evan is a helpful host with great communication. We hope to go back again. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.8 out of 10, Excellent, (16)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat

120 steps to beach! Safely on the beach side of the road!

9.8 out of 10, Exceptional, (183)
"We had a wonderful weekend here!"
120 steps to beach! Safely on the beach side of the road!

New luxury pool home, 2 min to beach, 360 water views, club available

9.8 out of 10, Exceptional, (107)
"Loved this Beach home! We had our entire family on this North Captiva trip, perfect beach house with pool, great space for everyone!! Close to all beaches with golf carts. Owners were awesome, fast replies! We could see the water from many rooms at the house!! Thank you!!"
New luxury pool home, 2 min to beach, 360 water views, club available

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.0 out of 10, Wonderful, (62)
"Loved our stay! "
The price is CA $152
CA $490 total
includes taxes & fees
Sep 5 - Sep 6
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (78)
"I loved the property and the host was also very professional. "
Paradise Cove at Lemon Bay

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (11)
"Nic place to stay and enjoy the area"
The price is CA $109
CA $744 total
includes taxes & fees
Aug 26 - Aug 27
Chadwick Cove Resort & Marina

BEAUTIFUL OCEANFRONT BEACH LOCATION - FALL SPECIALS!!!!

9.8 out of 10, Exceptional, (69)
"Great trip!"
BEAUTIFUL OCEANFRONT BEACH LOCATION - FALL SPECIALS!!!!

HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!

10.0 out of 10, Exceptional, (206)
"What a great place to stay and it is so well organized! This house does have everything! "
The price is CA $372
CA $770 total
includes taxes & fees
Aug 26 - Aug 27
HOT SALE Beautiful Villa Lake View Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!

Luxury GULF access! DOCK/SPA/Pool/GAME ROOM

10.0 out of 10, Exceptional, (22)
"Just a very welcoming home, making for an easy, relaxing spring break. Well maintained. Has all the amenities one could want or need. We felt very at home here. The kids were over the moon, being able to hang out and swim all day. Would book again!"
Luxury GULF access! DOCK/SPA/Pool/GAME ROOM

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

8.2 out of 10, Very good, (19)
"Overall good property. Clean and great location."
The price is CA $187
CA $616 total
includes taxes & fees
Aug 26 - Aug 27
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

BEACHFRONT, HEATED POOL, KAYAKS/SUP, LANAI W/ GULF VIEWS, 85' DOCK, 2 GOLF CARTS

9.8 out of 10, Exceptional, (169)
"Great location and always something to do including walking the beach and sitting by the pool."
BEACHFRONT, HEATED POOL, KAYAKS/SUP, LANAI W/ GULF VIEWS, 85' DOCK, 2 GOLF CARTS

4-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (138)
"Nice place very quiet location. Pool was great (Heated)Took about 5-8 min to get to the beach.Would stay again. Nick was an excellent host"
4-Bedroom Pool Home Convenient To Beaches

Captiva Beach Sunset: Gulf Front, Pool, NCIC, 2 Carts, Reserve Fall Dates Now!

9.8 out of 10, Exceptional, (70)
"What a great place and great hosts! First time for our group on North Captiva and it did not disappoint. Tons of wildlife, beautiful property, great fishing and great people. Will be back again!"
Captiva Beach Sunset: Gulf Front, Pool, NCIC, 2 Carts, Reserve Fall Dates Now!
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gasparilla Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gasparilla Island vacation rentals we have selected for you start as low as CA $109 per night. Entering your travel dates in the search wizard 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.