Search Vacation Homes in Longboat Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Vacation Homes in Longboat Key

A heated pool
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, (59)
"Clean, cozy and right in the beach!! Was a perfect little getaway! "
United States
Michelle M.
The price is SAR 585
SAR 1,253 total
includes taxes & fees
12 Dec - 13 Dec
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is SAR 486
SAR 1,304 total
includes taxes & fees
10 Dec - 11 Dec
Siesta Heron Suites & Villas
Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (51)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is SAR 375
SAR 975 total
includes taxes & fees
2 Dec - 3 Dec
Siesta Key Island Rentals
Beach
Waterfront Retreat — Canal front, Pool, Putting Green, Beach Gear — 2BR/2BA

Waterfront Retreat — Canal front, Pool, Putting Green, Beach Gear — 2BR/2BA

Bradenton
10.0 out of 10, Exceptional, (8)
"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 SAR 341
SAR 1,395 total
includes taxes & fees
14 Dec - 15 Dec
Waterfront Retreat — Canal front, Pool, Putting Green, Beach Gear — 2BR/2BA
Terrace/patio
The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)

Bradenton
10.0 out of 10, Exceptional, (168)
"perfect location and size for what we were looking for"
United States
michael w.
The price is SAR 446
SAR 960 total
includes taxes & fees
2 Dec - 3 Dec
The Hideaways at Point Pleasant (Palm Side)
Dining
[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway

Siesta Key
10.0 out of 10, Exceptional, (22)
"Great place and location"
United States
Karen A.
The price is SAR 348
SAR 1,115 total
includes taxes & fees
7 Dec - 8 Dec
[escape to paradise] siesta key beach getaway
Smart TV, stereo
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, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
United States
Kyle S.
The price is SAR 483
SAR 1,086 total
includes taxes & fees
2 Dec - 3 Dec
Charming home near Anna Maria Island with Jacuzzi
Property grounds
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, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is SAR 456
SAR 1,264 total
includes taxes & fees
9 Dec - 10 Dec
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Beach
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Sarasota
9.6 out of 10, Exceptional, (35)
"Great place, clean, fully stocked kitchen, very convenient location. Would definitely stay again."
United States
Nan G.
The price is SAR 540
SAR 1,804 total
includes taxes & fees
4 Dec - 5 Dec
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Exterior detail
Casa del Río! Beaches, IMG, Boating & Riverwalk.

Casa del Río! Beaches, IMG, Boating & Riverwalk.

River District
10.0 out of 10, Exceptional, (56)
"Everything was great. Very clean, very well-furnished and stocked. Great communication from the owner and easy to get in"
United States
Thomas S.
The price is SAR 321
SAR 1,576 total
includes taxes & fees
2 Dec - 3 Dec
Casa del Río! Beaches, IMG, Boating & Riverwalk.
Outdoor dining
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)
"Excellent for a family trip."
United States
RHEA
The price is SAR 371
SAR 1,843 total
includes taxes & fees
2 Dec - 3 Dec
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Outdoor dining
The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta

2.0 star property
Sarasota
10.0 out of 10, Exceptional, (2)
"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 SAR 431
SAR 775 total
includes taxes & fees
2 Dec - 3 Dec
The Mermaid at Tiny House Siesta
Smart TV, Netflix, streaming services
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, (16)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
The price is SAR 334
SAR 879 total
includes taxes & fees
2 Dec - 3 Dec
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
1 bedroom, iron/ironing board, travel crib, free WiFi
Tiny Carriage House, close to AMI, Bikes, walkable

Tiny Carriage House, close to AMI, Bikes, walkable

2.0 star property
Bradenton
10.0 out of 10, Exceptional, (10)
"Nice little spot close to downtown Bradenton. "
United States
Matt
The price is SAR 439
SAR 983 total
includes taxes & fees
8 Dec - 9 Dec
Tiny Carriage House, close to AMI, Bikes, walkable
Terrace/patio
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

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

Bradenton
9.4 out of 10, Exceptional, (67)
"Great place to stay!"
United States
Wendi B.
The price is SAR 338
SAR 520 total
includes taxes & fees
2 Dec - 3 Dec
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite
Fridge, microwave, oven, coffee/tea maker
Walk to Siesta key beach | Private Dock | Patio | Pool

Walk to Siesta key beach | Private Dock | Patio | Pool

Siesta Key Village
9.4 out of 10, Exceptional, (14)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is SAR 431
SAR 1,377 total
includes taxes & fees
2 Dec - 3 Dec
Walk to Siesta key beach | Private Dock | Patio | Pool
Beach
Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway

Bradenton
10.0 out of 10, Exceptional, (136)
"A great place to stay! They allowed us early check in which was great so we had ample time to settle in and prepare for the week. We had decided to eat in more and this was the perfect place for that! We were able to grill and cook, and hang out in the pool in a spacious backyard!"
United States
Andi J.
The price is SAR 500
SAR 1,424 total
includes taxes & fees
2 Dec - 3 Dec
Paradise Cove -- A perfect Beach Getaway
Outdoor dining
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, (18)
"Fun place "
United States
Maureen
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
Pool
Coastal Pool Bungalow - 15 Mins to Famous Beaches

Coastal Pool Bungalow - 15 Mins to Famous Beaches

Sarasota Springs
9.8 out of 10, Exceptional, (27)
"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 SAR 446
SAR 1,122 total
includes taxes & fees
15 Dec - 16 Dec
Coastal Pool Bungalow - 15 Mins to Famous Beaches
Beach
Little Charm-Close to Anna Maria Island-IMG Academy-Gt Bray Park

Little Charm-Close to Anna Maria Island-IMG Academy-Gt Bray Park

Bradenton
10.0 out of 10, Exceptional, (16)
"Comfy clean private house great neighborhood totally relaxing close to good resturants and beaches will book again."
United States
john l.
The price is SAR 450
SAR 1,141 total
includes taxes & fees
2 Dec - 3 Dec
Little Charm-Close to Anna Maria Island-IMG Academy-Gt Bray Park
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

10/10 Excellent
"Fantastic stay . All servers were great. Staff very friendly and helpful. "
Richard 1-night trip
Posted 13 hours ago
The St. Regis Longboat Key Resort