Search Villas in Gasparilla Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Villas in Gasparilla Island

Matlacha Tiny Village
Dock

Matlacha Tiny Village

3.0 star property
8.8 out of 10, Excellent, (259)
"Amazing little place. Not so little. Lovely. Excellent host and proximity to everything! "
The price is SAR 368
SAR 692 total
includes taxes & fees
31 Jul - 1 Aug
Matlacha Tiny Village
Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very Good, (77)
"The property was outstanding. The owners were marvelous would definitely go back."
Paradise Cove at Lemon Bay
Waterfront Mermaid's Retreat Delights!
Beach nearby, beach towels

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (65)
"Absolutely wonderful stay! I could’ve stayed another day to just do nothing. "
Waterfront Mermaid's Retreat Delights!
Waterfront Paradise Bay
A heated pool

Waterfront Paradise Bay

10.0 out of 10, Exceptional, (81)
"Really comfortable stay. Beautiful location. The pool was great and it’s such a short walk to the beach. Our family had a great time! "
Waterfront Paradise Bay
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
On the beach, sun loungers, beach towels

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

10.0 out of 10, Exceptional, (117)
"Beautiful and relaxing! We enjoyed our stay it was just what we needed."
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Villa Tropical Eden - Where Families & Furry Friends Feel at Home!
Fridge, microwave, oven, stovetop

Villa Tropical Eden - Where Families & Furry Friends Feel at Home!

Villa Tropical Eden - Where Families & Furry Friends Feel at Home!
VILLA SALTY ESCAPE - HEATED POOL | FAMILY FRIENDLY | BOAT RENTAL + TOURS VOUCHER INCL.
Fridge, microwave, oven, stovetop

VILLA SALTY ESCAPE - HEATED POOL | FAMILY FRIENDLY | BOAT RENTAL + TOURS VOUCHER INCL.

VILLA SALTY ESCAPE - HEATED POOL | FAMILY FRIENDLY | BOAT RENTAL + TOURS VOUCHER INCL.
Beautiful 3 Bedroom Vacation Home with Private Pool
Exterior

Beautiful 3 Bedroom Vacation Home with Private Pool

10.0 out of 10, Exceptional, (107)
"Beautiful house with everything we needed. Would definitely stay there again. "
Beautiful 3 Bedroom Vacation Home with Private Pool
Villa Rosalinda - Cape Coral's Best - Waterfront, Pool & Spa, Great Views, Dock
Outdoor pool, a heated pool

Villa Rosalinda - Cape Coral's Best - Waterfront, Pool & Spa, Great Views, Dock

10.0 out of 10, Exceptional, (106)
"The house was as pictured. Would definitely stay here again!"
Villa Rosalinda - Cape Coral's Best - Waterfront, Pool & Spa, Great Views, Dock
Boater's dream! Waterfront, pool large dock, tiki hut, pool, and sauna.
Smart TV, fireplace, printers

Boater's dream! Waterfront, pool large dock, tiki hut, pool, and sauna.

9.8 out of 10, Exceptional, (29)
"She has everything you need at her house! What a spot, we had the best time with 3 families. Can’t wait to book again!"
Boater's dream! Waterfront, pool large dock, tiki hut, pool, and sauna.
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
Marina

"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath

10.0 out of 10, Exceptional, (12)
"Our favorite place we have stayed at manasota key ever"
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
Luxury Home, southern exposure, heated pool & Spa, SW, gulf access
Dining

Luxury Home, southern exposure, heated pool & Spa, SW, gulf access

10.0 out of 10, Exceptional, (125)
"Loved the house & location. Would love to stay here again!"
Luxury Home, southern exposure, heated pool & Spa, SW, gulf access
2 Masters - Wellness - Steam Bath - Whirl-Pool - Hammock..
A heated pool

2 Masters - Wellness - Steam Bath - Whirl-Pool - Hammock..

9.8 out of 10, Exceptional, (26)
"Very nice house. Great communication "
2 Masters - Wellness - Steam Bath - Whirl-Pool - Hammock..
Awesome 3 br/ 2 bath waterfront villa w. heated pool, boat lift, tiki hut, bikes
Outdoor dining

Awesome 3 br/ 2 bath waterfront villa w. heated pool, boat lift, tiki hut, bikes

Awesome 3 br/ 2 bath waterfront villa w. heated pool, boat lift, tiki hut, bikes
Perfect for two! This Pretty villa with an Awesome View of the Gulf! A3411B
A heated pool

Perfect for two! This Pretty villa with an Awesome View of the Gulf! A3411B

4.0 star property
9.2 out of 10, Wonderful, (114)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our beachfront villa was lovely, clean and well-maintained. The staff at Palm Island Resort is fabulous and the fact that so many people have worked there for many years is a great indicator of what a great resort this is. We enjoyed every moment...
Perfect for two! This Pretty villa with an Awesome View of the Gulf! A3411B
SNOW BIRDS WELCOME! SUNSHINE AND HEATED POOL
Sun loungers, beach towels

SNOW BIRDS WELCOME! SUNSHINE AND HEATED POOL

9.6 out of 10, Exceptional, (115)
"The perfect place to get away from winter in Upper Michigan. We have come to love the Cape Coral area with great restaurants and attractions."
SNOW BIRDS WELCOME! SUNSHINE AND HEATED POOL
Villa Sun-Kissed: Where Sunshine Meets Luxury
A heated pool

Villa Sun-Kissed: Where Sunshine Meets Luxury

9.0 out of 10, Wonderful, (11)
"Beautiful location. House was perfect for our family. Jana was a pleasure to deal with. Highly recommend. "
Villa Sun-Kissed: Where Sunshine Meets Luxury
Villa South Palms returns! Gulf-access with Southwest facing pool is back!
Exterior

Villa South Palms returns! Gulf-access with Southwest facing pool is back!

4.0 star property
9.8 out of 10, Exceptional, (33)
"Wonderful mattress"
Villa South Palms returns! Gulf-access with Southwest facing pool is back!
4 bedrooms (2 MASTERBÄDER) in total 3 bathrooms SOUTH-facing large pool, boat dock fiber optic network
Smart TV, books, music library, stereo

4 bedrooms (2 MASTERBÄDER) in total 3 bathrooms SOUTH-facing large pool, boat dock fiber optic network

9.8 out of 10, Exceptional, (70)
"We loved the house and outdoor pool area. Great house with everything we needed. Great kitchen and the outdoor grill was great. Loved the southern exposer. Great TV’s and Wi-FI music in and outside. The beds were all comfortable. We would definitely stay in this house again. Easy check in and check out. "
4 bedrooms (2 MASTERBÄDER) in total 3 bathrooms SOUTH-facing large pool, boat dock fiber optic network
SEASIDE VILLA MANATEE BAY in quiet location on Pine Island
Fridge, microwave, oven, stovetop

SEASIDE VILLA MANATEE BAY in quiet location on Pine Island

9.6 out of 10, Exceptional, (21)
"Owner/Manager was very helpful and responsive!"
SEASIDE VILLA MANATEE BAY in quiet location on Pine 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your villa in Gasparilla Island with Expedia?
We think planning a vacation shouldn't be difficult, so if you're searching for villas at the right price, Expedia is here to help. Save those pennies and select an all-inclusive stay, or splurge on a 5-star villa to spoil your favorite people. Our handy filters make it easy to find a place in Gasparilla Island that fits your needs.
How can I find cheap villas in Gasparilla Island?
With Expedia's useful filter tool, sourcing cheap villas in Gasparilla Island is a breeze. To discover properties that'll make your wallet smile, fine-tune your search by budget, star rating and amenities.