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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Longboat Key holiday homes

On the beach, beach umbrellas

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, (63 reviews)
"We had the most wonderful stay despite the cold temps for most it! The staff at our location are above and beyond to make sure you have everything you need! Highly recommend!"
United States
Sahra S.
The price is HK$1,223
HK$2,617 total
includes taxes & fees
4 Jun - 5 Jun
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Shower, hair dryer, towels

Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is HK$1,004
HK$2,153 total
includes taxes & fees
3 Jun - 4 Jun
Lakeview Bradenton Rental Near Beaches & IMG
Fridge, microwave, oven, stovetop

Casa Esquina – St. Pete | Near Beaches & Downtown

Casa Esquina – St. Pete | Near Beaches & Downtown
Greater Pinellas Point
The price is HK$940
HK$2,681 total
includes taxes & fees
9 Jun - 10 Jun
Casa Esquina – St. Pete | Near Beaches & Downtown
Beach towels

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 HK$1,068
HK$3,635 total
includes taxes & fees
7 Jun - 8 Jun
Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
Sun-loungers

"Manatee" 3 miles to Anna Marie<br>

"Manatee" 3 miles to Anna Marie<br>
Bradenton
9.8 out of 10, Exceptional, (18 reviews)
"Everything was great!!"
United States
Jean S.
The price is HK$1,489
HK$3,075 total
includes taxes & fees
4 Jun - 5 Jun
"Manatee" 3 miles to Anna Marie<br>
Fridge, microwave, oven, stovetop

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, (25 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is HK$735
HK$1,881 total
includes taxes & fees
3 Jun - 4 Jun
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
Fridge, microwave, oven, stovetop

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Large pool/spa home minutes from beach with arcade games and canal for fishing.
Palma Sola
9.4 out of 10, Exceptional, (81 reviews)
"Host was very welcoming and their home was absolutely stunning. We had the best time enjoying the space. Thank you!!"
United States
Valerie S.
The price is HK$2,716
HK$6,194 total
includes taxes & fees
8 Jun - 9 Jun
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Living area

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (43 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$994
HK$2,699 total
includes taxes & fees
3 Jun - 4 Jun
Siesta Heron Suites & Villas
Terrace/patio

The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (177 reviews)
"Great location. Super quiet! "
United States
John R.
The price is HK$940
HK$2,023 total
includes taxes & fees
6 Jun - 7 Jun
The Hideaways at Point Pleasant (Pine Side)
Property grounds

Cottage on the canal

Cottage on the canal
Bradenton
10.0 out of 10, Exceptional, (159 reviews)
"Clean and very nice. Would stay here again."
United States
Robert J.
The price is HK$2,359
HK$4,746 total
includes taxes & fees
8 Jun - 9 Jun
Cottage on the canal
Outdoor dining

Private Heated Pool Home on the bayou leading to the Gulf of Mexico☼

Private Heated Pool Home on the bayou leading to the Gulf of Mexico☼
Palma Sola
9.6 out of 10, Exceptional, (143 reviews)
"Good location, house was in great shape with all the essentials. Enjoyed the pool and morning coffee on the dock. "
United States
Gregory P.
The price is HK$2,116
HK$5,430 total
includes taxes & fees
8 Jun - 9 Jun
Private Heated Pool Home on the bayou leading to the Gulf of Mexico☼
Exterior

The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (176 reviews)
"Total class & hospitality!"
United States
Ronald P.
The price is HK$940
HK$2,007 total
includes taxes & fees
3 Jun - 4 Jun
The Hideaways at Point Pleasant (Palm Side)
Fridge, microwave, oven, stovetop

5 min drive to AMI•Free Heated Pool•Hot Tub•Near IMG•Fire Pit•Full Kitchen

5 min drive to AMI•Free Heated Pool•Hot Tub•Near IMG•Fire Pit•Full Kitchen
Bradenton
9.8 out of 10, Exceptional, (26 reviews)
"We were in town for a soccer tournament. This place was close, very clean, comfortable, and had a lot of amenities. We would absolutely stay there again!!"
United States
Patrick R.
5 min drive to AMI•Free Heated Pool•Hot Tub•Near IMG•Fire Pit•Full Kitchen
Beach nearby

Private family pool home, Outdoor Kitchen, Fire Pit, Pets OK, Near Anna Maria

Private family pool home, Outdoor Kitchen, Fire Pit, Pets OK, Near Anna Maria
Bradenton
10.0 out of 10, Exceptional, (81 reviews)
"Great property and very attentive hosts ! My crew had a great time and hope to book again soon."
United States
ON313 J.
Private family pool home, Outdoor Kitchen, Fire Pit, Pets OK, Near Anna Maria
Beach

Funky Flamingo! Beach Gear and Heated Pool

Funky Flamingo! Beach Gear and Heated Pool
Bradenton
9.6 out of 10, Exceptional, (14 reviews)
"Our stay at funky flamingo was excellent. The hosts were very responsive, the house was well equipped and the location was perfect "
United States
Maureen B.
Funky Flamingo! Beach Gear and Heated Pool
Beach nearby

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (31 reviews)
"We loved the location. It was in a very nice quiet neighborhood with a very short walk to the beach and main boulevard where are the shops and restaurants were located. The condo is very well maintained and has all the necessary amenities. We will definitely stay at this property next time we are in the area."
United States
Miroslawa
The price is HK$2,593
HK$5,240 total
includes taxes & fees
3 Jun - 4 Jun
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Terrace/patio

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, (79 reviews)
"It was very clean, appreciated that. "
United States
Juanita D.
The price is HK$868
HK$1,447 total
includes taxes & fees
3 Jun - 4 Jun
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Outdoor pool, a heated pool

"Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (33 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
The price is HK$1,489
HK$2,881 total
includes taxes & fees
14 Jun - 15 Jun
"Stingray" 3 miles to Anna Marie
Beach

Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway
Bradenton
10.0 out of 10, Exceptional, (147 reviews)
"Great property, wonderful and responsive host"
United States
Erik H.
The price is HK$1,820
HK$3,938 total
includes taxes & fees
9 Jun - 10 Jun
Paradise Cove -- A perfect Beach Getaway
Outdoor dining

Sun-Soaked & Heated Pool Home - Minutes to Siesta Key

Sun-Soaked & Heated Pool Home - Minutes to Siesta Key
South Sarasota
9.8 out of 10, Exceptional, (39 reviews)
"We enjoyed our stay very much. The kitchen was well stocked. The location was close to the beach and to the Crosley Powell estate where we were attending a wedding."
United States
Julie H.
The price is HK$2,144
HK$6,324 total
includes taxes & fees
29 Jun - 30 Jun
Sun-Soaked & Heated Pool Home - Minutes to Siesta Key
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.
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Top Longboat Key Hotel Reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

10/10 Excellent
"The view from out place was spectacular! We loved being able to sit out on the balcony and enjoy the beauty of the beach and ocean. Dinners out there -watching the sunset will be forever a favorite memory. "
Lisa B. 6-night trip
Posted 12 hours ago
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Find out more about Longboat Key

Longboat Key Vacation Homes information

Number of reviews
1,096
Accommodation
159 Vacation Homes
Lowest Price
HK$1,447
Highest Price
HK$6,324

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