Photo by Tom Hunt

Search Vacation Homes in Little 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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Little Gasparilla Island

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

9.8 out of 10, Exceptional, (103)
"Owners & property managers were amazing & responsive. Beautiful home & location "
New luxury pool home, 2 min to beach, 360 water views, club available

Wonderful pool home w screened lanai. Well maintained clean quiet Great location

9.8 out of 10, Exceptional, (89)
"The house is very clean and stocked with everything you need for a nice vacation. The owners have gone out of their way to make sure the guests have a good experience and even supplied beach accessories. The pool area was fantastic after a long day in the sun, clean and well maintained. We will stay at this home again when we’re in the area."
Wonderful pool home w screened lanai. Well maintained clean quiet Great location

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

9.8 out of 10, Exceptional, (172)
"Very nice accommodations in a very comfortable area. Easy beach access and within walking distance to restaurants."
The price is ¥33,608
¥70,085 total
includes taxes & fees
Jul 2 - Jul 3
120 steps to beach! Safely on the beach side of the road!

3 miles to beach, hot tub & fenced yard for pup

9.8 out of 10, Exceptional, (17)
"Great clean well appointed home with Relaxing Hot Tub and private fully fenced in yard. All as advertised...definitely would stay again! "
3 miles to beach, hot tub & fenced yard for pup

Coastal duplex with private beach access & deck - dog-friendly

7.2 out of 10, Good, (5)
"across the street from the beach."
Coastal duplex with private beach access & deck - dog-friendly

Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!

9.8 out of 10, Exceptional, (53)
"Very accommodating, very helpful , great communication, quickly responded to our needs."
The price is ¥14,273
¥46,860 total
includes taxes & fees
Jul 1 - Jul 2
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!

Comfy private home In Venice, Florida - Heated Pool, Minutes From the Beach

9.8 out of 10, Exceptional, (148)
"Wonderful home and host. Just minutes from beaches. Great time had by all. "
Comfy private home In Venice, Florida - Heated Pool, Minutes From the Beach

Beautiful House 🏖️ Newly Renovated Jan 2025😀Kayaks, Bikes,Beach Chairs,Fire Pit

10.0 out of 10, Exceptional, (66)
"Loved our stay "
Beautiful House 🏖️ Newly Renovated Jan 2025😀Kayaks, Bikes,Beach Chairs,Fire Pit

7BR, 3BA, Sleeps 17 near Englewood Beach, Manasota Key

10.0 out of 10, Exceptional, (13)
"Loved the location and having a dock, we rented a boat and had a great time exploring the area. The house easily handled our group of 9. Would stay here again!"
7BR, 3BA, Sleeps 17 near Englewood Beach, Manasota Key

Bohemian Sunrise

10.0 out of 10, Exceptional, (86)
"Great place"
Bohemian Sunrise

House with solar heated pool and lake view!

10.0 out of 10, Exceptional, (100)
"Nice location, relaxing view of lake. Comfortable bed and furniture. "
House with solar heated pool and lake view!

5 O'clock Somewhere

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ¥14,534
¥42,836 total
includes taxes & fees
Jun 23 - Jun 24
5 O'clock Somewhere

Dog-friendly retreat with enclosed lanai, pool, & grill - great central location

8.6 out of 10, Excellent, (7)
"The carpet in master bedroom is stained. Grouting in bathroom had some mold. Pool deck and patio furniture need power washed. The location was great - convenient to restaurants and shopping. Pool was wonderful once it heated up. Nice basic house but could use some cleaning and paint. "
Dog-friendly retreat with enclosed lanai, pool, & grill - great central location

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 **

NEW LISTING! OCEAN PARADISE: BEACHFRONT, SLEEPS 12, 2 CARTS, POOL, GAMES, & FUN

8.8 out of 10, Excellent, (8)
"The proprerty was great with a few minor hiccups but nothing major. We would definitely come back again."
NEW LISTING! OCEAN PARADISE: BEACHFRONT, SLEEPS 12, 2 CARTS, POOL, GAMES, & FUN

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

8.0 out of 10, Very Good, (12)
"The home was great, it had everything we needed for our stay. "
The price is ¥25,461
¥71,538 total
includes taxes & fees
Jul 7 - Jul 8
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, (165)
"The house and property exceeded expectations. Kitchen was well stocked and has everything you would need for preparing meals for a week. The pool was clean and warm which the kids used every day. The golf carts provided are like new and great for getting around the island. We used the grocery order service mid week and had everything the next day, very convenient. I would highly recommend staying at this location, you wont be disappointed. "
BEACHFRONT, HEATED POOL, KAYAKS/SUP, LANAI W/ GULF VIEWS, 85' DOCK, 2 GOLF CARTS

Salty Mermaid. Beach House on Little Gasparilla Island. Come get salty!

10.0 out of 10, Exceptional, (3)
"Perfect house on LGI. Zero complaints "
Salty Mermaid. Beach House on Little Gasparilla Island. Come get salty!

Beautiful Island Home, Private Pool, Steps from Beach, Golf Cart; Like New!

10.0 out of 10, Exceptional, (8)
The price is ¥72,600
¥189,829 total
includes taxes & fees
Jul 19 - Jul 20
Beautiful Island Home, Private Pool, Steps from Beach, Golf Cart; Like New!

HAPPY FUN BLUE HOUSE kids, pets friendly, 3 miles away from the beach🏖️.

9.8 out of 10, Exceptional, (45)
"We loved the location. There’s tons of beaches and miles of hiking trails close by. The giant backyard was great for our dogs as was the dog beach and two dog parks close by. The house was very clean. The hostess communicated with me very quickly about checkin and a minor repair we found when we arrived. We didn’t use the pool but it looked nice. We will come again we hope. "
HAPPY FUN BLUE HOUSE kids, pets friendly, 3 miles away from the beach🏖️.
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