Search Vacation Homes in Longboat Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Longboat Key vacation homes

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Clean, cozy and right in the beach!! Was a perfect little getaway! "
United States
Michelle M.
The price is ¥22,301
¥48,473 total
includes taxes & fees
Apr 16 - Apr 17
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Cottage on the canal

Cottage on the canal
Bradenton
10.0 out of 10, Exceptional, (153 reviews)
"It a was bigger place then in the pictures, it allow us to have a short visit with family over Christmas. "
United States
Ryan B.
The price is ¥47,493
¥95,664 total
includes taxes & fees
Apr 16 - Apr 17
Cottage on the canal

Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway
Bradenton
10.0 out of 10, Exceptional, (141 reviews)
"Great property, wonderful and responsive host"
United States
Erik H.
The price is ¥25,446
¥66,414 total
includes taxes & fees
Apr 19 - Apr 20
Paradise Cove -- A perfect Beach Getaway

Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool, Outdoor Kitchen, and Fire Pit

Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool, Outdoor Kitchen, and Fire Pit
Bradenton
10.0 out of 10, Exceptional, (77 reviews)
"Absolutely love this place, nice and kind tucked away but two minutes from the beach, the pool and the outdoor grilling area made it totally worth it "
United States
Robert M.
The price is ¥38,280
¥100,938 total
includes taxes & fees
Apr 23 - Apr 24
Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool, Outdoor Kitchen, and Fire Pit

"Manatee" 3 miles to Anna Marie<br>

"Manatee" 3 miles to Anna Marie<br>
Bradenton
9.8 out of 10, Exceptional, (18 reviews)
"Great location - near the beach and IMG Academy. Quiet street. Ease of check in/out. Pool Was very relaxing. "
United States
Janine
The price is ¥30,180
¥61,837 total
includes taxes & fees
Apr 26 - Apr 27
"Manatee" 3 miles to Anna Marie<br>

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.4 out of 10, Exceptional, (74 reviews)
"Very clean, the host was very good at communication. We were there for an event so we wouldn't have to drive back to Tampa. It was a seamless stay. The host had snacks and small fridge and freezer, coffee maker, air fryer and microwave. It was a older and a little dated, but clean and just what we needed. We would stay again."
United States
Paul Vance R.
The price is ¥17,584
¥29,329 total
includes taxes & fees
Apr 16 - Apr 17
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
Bradenton
10.0 out of 10, Exceptional, (14 reviews)
"Great spot, lovely back yard and pool, so relaxing we loved it."
United States
Cadence
The price is ¥12,985
¥62,310 total
includes taxes & fees
Apr 16 - Apr 17
Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

"Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (31 reviews)
" Clean, easy to get to, well stocked with towels, beach towels, etc. Gorgeous outdoor seating and pool. Would stay again. "
United States
Danielle W.
The price is ¥30,180
¥55,685 total
includes taxes & fees
Apr 30 - May 1
"Stingray" 3 miles to Anna Marie

Pickleball, Game Room, Heated Pool, 4 Min to Beach

Pickleball, Game Room, Heated Pool, 4 Min to Beach
Bradenton
10.0 out of 10, Exceptional, (19 reviews)
"Loved this property, one of the best that we have stayed at, very close to the beach and restaurants."
United States
Ana Maria
The price is ¥70,207
¥150,092 total
includes taxes & fees
Apr 28 - Apr 29
Pickleball, Game Room, Heated Pool, 4 Min to Beach

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (182 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
The price is ¥22,587
¥58,005 total
includes taxes & fees
Apr 16 - Apr 17
Paradise Retreat with HEATED POOL-- Need We Say More

Heated saltwater pool + bubbling hot tub + cozy massage chair

Heated saltwater pool + bubbling hot tub + cozy massage chair
Bradenton
10.0 out of 10, Exceptional, (26 reviews)
"All of it. The host is awesome…."
United States
Randall R.
The price is ¥42,445
¥103,323 total
includes taxes & fees
Apr 16 - Apr 17
Heated saltwater pool + bubbling hot tub + cozy massage chair

Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12
Central Sarasota
9.8 out of 10, Exceptional, (16 reviews)
"Great place perfect location to the marina, and downtown area. Highly recommended thanks "
United States
Domingo B.
The price is ¥33,356
¥75,290 total
includes taxes & fees
Apr 16 - Apr 17
Luxury House Walking Distance to Ocean - Sleeps 12

The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (177 reviews)
"The property is nice and comfortably equipped. The location is very good."
United States
carlos b.
The price is ¥19,045
¥40,995 total
includes taxes & fees
Apr 19 - Apr 20
The Hideaways at Point Pleasant (Pine Side)

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
River District
10.0 out of 10, Exceptional, (67 reviews)
"Awesome location, beautiful house, wonderful host."
United States
Michele D.
The price is ¥20,729
¥61,824 total
includes taxes & fees
Apr 20 - Apr 21
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

Centrally Located, Sarasota Home Close To Amish Community

Centrally Located, Sarasota Home Close To Amish Community
Sarasota Springs
10.0 out of 10, Exceptional, (173 reviews)
"This home was amazing! Honestly felt at home the moment I walked in. Everything you could need for your stay was provided. Very clean, great host. I'll be back!"
United States
Maudi B.
The price is ¥24,620
¥62,789 total
includes taxes & fees
Apr 16 - Apr 17
Centrally Located, Sarasota Home Close To Amish Community

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (36 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is ¥45,010
¥81,343 total
includes taxes & fees
Apr 29 - Apr 30
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (65 reviews)
"We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars! "
United States
Laura
The price is ¥28,706
¥65,469 total
includes taxes & fees
Apr 20 - Apr 21
Siesta Key Island Rentals

The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (174 reviews)
"perfect location and size for what we were looking for"
United States
michael w.
The price is ¥19,045
¥40,201 total
includes taxes & fees
Apr 20 - Apr 21
The Hideaways at Point Pleasant (Palm Side)

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (13 reviews)
"We enjoyed our stay at Everglades Villa. The location was the best feature as we were able to walk to Siesta Key Village and the beach. "
United States
Lisa S.
The price is ¥27,583
¥76,237 total
includes taxes & fees
Apr 16 - Apr 17
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba

Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba
Siesta Key Village
9.6 out of 10, Exceptional, (57 reviews)
"What a beautiful place in an excellent location central to everything!! We loved the house and would absolutely stay here again if we make it back to vacation in Siesta Key!"
United States
Mandy H.
The price is ¥55,594
¥165,859 total
includes taxes & fees
Apr 16 - Apr 17
Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba
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

Top Longboat Key Hotel Reviews

Find out more about Longboat Key

Longboat Key Vacation Homes information

Number of reviews
1,518
Accommodation
158 Vacation Homes
Lowest Price
¥29,329
Highest Price
¥165,859