Holiday 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 holiday homes

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is €333
includes taxes & fees
18 Jan - 19 Jan
Siesta Heron Suites & Villas

Waterfront Cottage w/Pool, Putting Green & Florida Room—Near AMI Beaches-2BR/2BA

Waterfront Cottage w/Pool, Putting Green & Florida Room—Near AMI Beaches-2BR/2BA
Bradenton
10.0 out of 10, Exceptional, (11 reviews)
"Cottage cheese as wonderful It had everything we could possibly need and more. Very relaxing and comfortable and accommodating. Hostess was responsive and attentive. Hope to have an opportunity to stay again!!"
United States
Wendy
The price is €350
includes taxes & fees
18 Jan - 19 Jan
Waterfront Cottage w/Pool, Putting Green & Florida Room—Near AMI Beaches-2BR/2BA

Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
10.0 out of 10, Exceptional, (6 reviews)
"Easy to check in, clean and comfortable "
United States
Hugo J.
The price is €191
includes taxes & fees
2 Feb - 3 Feb
Charming 2-bedroom house in lovely Sarasota with yard.

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
2.0 star property
Sabal Harbour
10.0 out of 10, Exceptional, (22 reviews)
"Everything was great!"
United States
Lisa and Colin M.
The price is €301
includes taxes & fees
19 Jan - 20 Jan
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Beautiful Blue Beach House Kids & Pets OK! MARCH 2026 SPECIALS!

Beautiful Blue Beach House Kids & Pets OK! MARCH 2026 SPECIALS!
Bradenton
10.0 out of 10, Exceptional, (33 reviews)
"Our first week long vacation as a family!!! It was an amazing experience. The house is right where you want to be. Closely and conveniently located to all the local restaurants and shopping areas, while being minutes away from the beach. It was an amazing experience!"
United States
Crystal E.
The price is €511
includes taxes & fees
2 Feb - 3 Feb
Beautiful Blue Beach House Kids & Pets OK! MARCH 2026 SPECIALS!

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
2.0 star property
Sarasota
10.0 out of 10, Exceptional, (2 reviews)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is €183
includes taxes & fees
18 Jan - 19 Jan
The Mermaid at Tiny House Siesta

The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (169 reviews)
"perfect location and size for what we were looking for"
United States
michael w.
The price is €217
includes taxes & fees
9 Feb - 10 Feb
The Hideaways at Point Pleasant (Palm Side)

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Sarasota
9.4 out of 10, Exceptional, (17 reviews)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
The price is €211
includes taxes & fees
2 Feb - 3 Feb
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Sunny Shores
9.4 out of 10, Exceptional, (35 reviews)
"Excellent for a family trip."
United States
RHEA
The price is €454
includes taxes & fees
16 Jan - 17 Jan
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

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, (67 reviews)
"Great place to stay!"
United States
Wendi B.
The price is €138
includes taxes & fees
27 Jan - 28 Jan
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

"Manatee" 3 miles to Anna Marie<br>

"Manatee" 3 miles to Anna Marie<br>
Bradenton
9.8 out of 10, Exceptional, (17 reviews)
"Great location and really nice pool. Had a great week here, easy to get to the island and also close to shopping and dining."
United States
Matthew H.
The price is €316
includes taxes & fees
18 Jan - 19 Jan
"Manatee" 3 miles to Anna Marie<br>

Charming home near Anna Maria Island with Jacuzzi

Charming home near Anna Maria Island with Jacuzzi
2.0 star property
Bradenton
10.0 out of 10, Exceptional, (15 reviews)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
United States
Kyle S.
The price is €243
includes taxes & fees
29 Jan - 30 Jan
Charming home near Anna Maria Island with Jacuzzi

Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe

Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe
Anna Maria
9.6 out of 10, Exceptional, (31 reviews)
"Amities were scarce. House holds 6 ppl, 4 beach chairs. One roll of tp and one hand soap for each bath including shower. "
United States
William
Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (24 reviews)
"Clean and comfortable. "
United States
Laney
The price is €307
includes taxes & fees
27 Jan - 28 Jan
[escape to paradise] siesta key beach getaway

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (19 reviews)
"Fun place "
United States
Maureen
The price is €242
includes taxes & fees
19 Jan - 20 Jan
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (69 reviews)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Coastal Pool Bungalow - 15 Mins to Famous Beaches

Coastal Pool Bungalow - 15 Mins to Famous Beaches
Sarasota Springs
9.8 out of 10, Exceptional, (30 reviews)
"The house was great and everything was well equipped. The area is nice and the famous beaches are just a short drive away. I fully recommend this house although it was a bit pricey during our stay"
Germany
Alina L.
The price is €284
includes taxes & fees
19 Jan - 20 Jan
Coastal Pool Bungalow - 15 Mins to Famous Beaches

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
The price is €413
includes taxes & fees
26 Jan - 27 Jan
Beachy Sarasota Duplex

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, (60 reviews)
"We loved this cottage and will be back!"
United States
Brenda D.
The price is €333
includes taxes & fees
19 Jan - 20 Jan
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
The price is €526
includes taxes & fees
25 Jan - 26 Jan
Lulu's Key House Leatherback 2/2 Downstairs
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 Holiday Homes information

Number of reviews
657
Accommodation
172 Holiday Homes
Lowest Price
€138
Highest Price
€526