Search Vacation Homes in Gasparilla Island

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 1009 Vacation Homes in Gasparilla Island with updated reviews, rates, and availability.

Gorgeous Pool house 5 min from the beach, shopping and restaurants I
Living area
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
9.2 out of 10, Wonderful, (34)
"This was a great home to stay in! My friend and I were in town for a birthday. The neighborhood is very safe and close to so many local spots. The owners were very responsive and helpful. "
The price is SAR 376
SAR 1,285 total
includes taxes & fees
8 Nov - 9 Nov
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
West facing sun in pool allows for great shade under cover for those hot days
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
10.0 out of 10, Exceptional, (37)
"Beautiful property, spacious , nice area , quiet, very nice amenities. Love the atmosphere:) will be back again "
Western Exposure on cul-de-sac with spill over spa pool & boat dock. SUNSETS!
Beautiful Villa Lake View! Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
Beautiful Villa Lake View!
Beautiful Villa Lake View! Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
10.0 out of 10, Exceptional, (186)
"Our absolute favorite vacation spot. Sondra and Bob are the best hosts, great communication and a wonderful property. "
Beautiful Villa Lake View! Heated Pool, Spa & Kayak’s🐠 Simply Wonderful!
Modern canal-front luxury with pool, patio, grill, dock, Ping-Pong, AC, & WiFi
Modern canal-front luxury with pool, patio, grill, dock, Ping-Pong, AC, & WiFi
9.2 out of 10, Wonderful, (17)
"We have stayed in multiple homes in Cape Coral over the years for baseball and this one was definitely one of the best. I will be staying here again! Beautifully decorated, all the necessities needed (plus more), had a great layout, easy check in and check out process, and top-notch communication! Plus, if you need anything during your stay, you simply text and they make sure it is taken care of. Especially for the price, I highly suggest this home for your stay. It is a Cape Coral Treasure!"
Modern canal-front luxury with pool, patio, grill, dock, Ping-Pong, AC, & WiFi
Blue Pineapple Delight
Exterior
Blue Pineapple Delight
10.0 out of 10, Exceptional, (11)
"I am working nearby this summer and needed a safe, pet-friendly and spacious cottage to stay. This checked all the boxes and the owner was very gracious with checking in/out dates. I even picked a fresh pineapple out of the front yard to eat! It’s an “old Florida” vibe in the neighborhood, super close to beach area and next to a Boy Scout lodge. As a female traveling with my daughter I felt safe. The washer/dryer was appreciated! We enjoyed the screened porch in the evenings. The cottage is very...
Blue Pineapple Delight
Modern Clean & Fully-Stocked Luxury Pool Home on Canal
Modern Clean & Fully-Stocked Luxury Pool Home on Canal
10.0 out of 10, Exceptional, (25)
"We really enjoyed our stay at this property. The house is very nice and well-equipped. The neighborhood is great and centrally located. We hope to return!"
Modern Clean & Fully-Stocked Luxury Pool Home on Canal
Punta Gorda Oasis w/ Saltwater Pool + Gas Grill!
Punta Gorda Vacation Rental | 3BR | 2BA | Step-Free Access | 1,392 Sq Ft
Punta Gorda Oasis w/ Saltwater Pool + Gas Grill!
10.0 out of 10, Exceptional, (13)
"We had a lovely time. Our older son lives nearby and his family came to visit during the day. We used the pool a lot! "
Punta Gorda Oasis w/ Saltwater Pool + Gas Grill!
Palm Island / Don Pedro Island beach house with POOL! [Pet-Friendly]
Beautiful island beach home
Palm Island / Don Pedro Island beach house with POOL! [Pet-Friendly]
10.0 out of 10, Exceptional, (125)
"We loved our stay at Terrapins Hideaway. I only wish we could have stayed longer!!!"
Palm Island / Don Pedro Island beach house with POOL! [Pet-Friendly]
Sought after SW Cape Coral in beautiful waterfront neighborhood
Pool
Sought after SW Cape Coral in beautiful waterfront neighborhood
9.6 out of 10, Exceptional, (43)
"Great communication with the host. Comfortable house and neighborhood. Excellent pool. Nice fenced in yard. And don’t worry when you reserve it and they send a message that says you aren’t allowed to turn the AC below 73 degrees. We like it cool and it was perfectly cool in the house!"
Sought after SW Cape Coral in beautiful waterfront neighborhood
Pool Side Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES
Pool
Pool Side Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES
10.0 out of 10, Exceptional, (66)
"We had a very nice and comfortable time at Pete’s house. Very nice & clean. The pool & the jacuzzi were wonderful. We’d be back! Thanks! "
Pool Side Paradise in Southwest Cape Coral NO DAMAGE FROM HURRICANES
Pool, Spa, Kayaks, Bikes, Fishing gear & more
Paradise awaits
Pool, Spa, Kayaks, Bikes, Fishing gear & more
10.0 out of 10, Exceptional, (111)
"Beautiful setting, outside area is fab. Inside well laid out and family oriented "
Pool, Spa, Kayaks, Bikes, Fishing gear & more
NEW LISTING! BEACH PARADISE: BEACHFRONT, SLEEPS 10, 2 CARTS, POOL, GAMES, & FUN
Exterior
NEW LISTING! BEACH PARADISE: BEACHFRONT, SLEEPS 10, 2 CARTS, POOL, GAMES, & FUN
10.0 out of 10, Exceptional, (5)
"Third stay at this property. Property is well managed by Shelly’s Seashell Properties. They were attentive and responded quickly to all our requests. House was well equipped and was perfect for our group of 10."
NEW LISTING! BEACH PARADISE: BEACHFRONT, SLEEPS 10, 2 CARTS, POOL, GAMES, & FUN
Walkout to the Beach! Beautiful Setting on the Gulf! Amazing Sunsets!
Exterior
Walkout to the Beach! Beautiful Setting on the Gulf! Amazing Sunsets!
9.0 out of 10, Wonderful, (51)
"We loved our stay. Everything was perfect. Highly recommend!"
Walkout to the Beach! Beautiful Setting on the Gulf! Amazing Sunsets!
LUXURY WATERFRONT! WARM PRIVATE POOL! MIN TO BEACHES! WIFI! GRILL! BABY SUPPLIES
This is a loved hangout spot. You can watch your young swimmers or a boat go by.
LUXURY WATERFRONT! WARM PRIVATE POOL! MIN TO BEACHES! WIFI! GRILL! BABY SUPPLIES
9.6 out of 10, Exceptional, (144)
"The property was as described! "
LUXURY WATERFRONT! WARM PRIVATE POOL! MIN TO BEACHES! WIFI! GRILL! BABY SUPPLIES
See all that Southwest Florida has to offer!
Exterior
See all that Southwest Florida has to offer!
10.0 out of 10, Exceptional, (8)
"It was a pleasant place to stay. We were there about a month. The host is extremely responsive and helpful. Couldn't ask for more!"
See all that Southwest Florida has to offer!
INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY
Incredible home is surrounded by large palms and tropical landscaping.
INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY
10.0 out of 10, Exceptional, (31)
"Super clean, comfortable, spacious, awesome neighborhood. Beautiful home."
INCREDIBLE WATER VIEW!! NEW LUXURY REMODELED HOME; HEATED SALT POOL, GOLF NEARBY
Quaint heated pool home minutes away from the beach!
Living area
Quaint heated pool home minutes away from the beach!
10.0 out of 10, Exceptional, (13)
"The home is very comfortable and clean. The kitchen is fully stocked with everything you need. Layout is very good. The pool was a perfect temperature everyday. Plenty of space. Very homey ."
Quaint heated pool home minutes away from the beach!
Casa Sangria Delights
Just 2 minute walk to absolutely breathtaking sunsets!
Casa Sangria Delights
9.4 out of 10, Exceptional, (161)
"Super cute little cottage that was perfectly located on the key !! This key is my happy place and now my freind’s as well ! The walkability to the beach and restaurants is perfect from the cottage !! The pool is a big bonus too on the warmer days when you just don’t want to get sandy…5 stars all around!!!"
Casa Sangria Delights
Cape Escape is the perfect name for this place..
Exterior detail
Cape Escape is the perfect name for this place..
10.0 out of 10, Exceptional, (36)
"Such a beautiful home. The backyard views were breathtaking. Especially around sunset time. The host was very good at responding back with any questions I had. The home looks exactly like it looks in the pictures. I live in the area so it was more of a staycation for me but I had family from the east coast of Florida come and visit. We used the kayaks and it was so much fun. We saw a few turtles in the water super cute! Would definitely recommend and stay again in the future. "
Cape Escape is the perfect name for this place..
Florida Gulf Coast Getaway: Pool + Screened Lanai!
Rotonda West Vacation Rental | 4BR | 2BA | 1,820 Sq Ft | 1 Step Required
Florida Gulf Coast Getaway: Pool + Screened Lanai!
9.6 out of 10, Exceptional, (7)
"Had a fairly nice stay, extenuating circumstances aside. (visit ended up being bookended by 2 major storms) My main pain points came down to the pool area being rather dirty, with algae and slime on large portions of the patio. Also, I had some chats with the host prior to arriving about the state of beaches in the area... i was told that the beaches had some limited access, but that most were accessible. However, upon arriving, *all* beaches in the area were completely closed off. I am a...
Florida Gulf Coast Getaway: Pool + Screened Lanai!
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.
Don't see what you're looking for?
See all available properties in Gasparilla Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Gasparilla Island

The Suites at Fishermen’s Village- 2 Bedroom Suites
Exterior
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (663)
"This is such a great place to stay especially for families that need space and a kitchen. We love it here. Just wish the pool area was a little nicer. "
The price is SAR 869
SAR 956 total
includes taxes & fees
13 Nov - 14 Nov
The Suites at Fishermen’s Village- 2 Bedroom Suites
Matlacha Tiny Village
Room
Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (238)
"Quiet area and great little houses. Rented the margarita and was not disappointed. At one point our door lock failed and the manager was there within a few minutes to fix it. Would stay again!"
Matlacha Tiny Village
Privacy in Paradise
Exterior
Privacy in Paradise
10.0 out of 10, Exceptional, (61)
"The property was more beautiful than we expected. There was more than enough space to lounge eat or relax. It was so clean we didn’t use the linens or pillows we brought with us. Anything we forgot to bring was in the pantry! And which host leaves us sodas, water and a bottle of great wine?… Richard! We didn’t want to leave and have decided to return in the spring, summer and fall next year. Thanks for treating us so well. Bravo Paradise!!"
Privacy in Paradise
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.