Vacation rentals in Longboat Key

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Top-rated vacation rentals in Longboat Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Longboat Key
Summer House longboat key
Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle
4.86 out of 5 average rating, 103 reviews
Guest favourite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Check our nearby sister property for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, check out our VIDEOS!
Nov. 5 – 12
$883 CAD per night
4.98 out of 5 average rating, 296 reviews
Guest favourite
Townhouse in Longboat Key
Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse
Kick back and relax in this calm, stylish space. In Cedars East, across from beach AND on the bay. Sleeps 6 - king size master and queen bed upstairs, sofa bed. All new carpets upstairs and full laundry in the unit too! Lovely enclosed balcony overlooking trees and boardwalk. Couple of trek bikes in the garage- 10 min walk/ 3 min cycle to beach. Large shared swimming pool, tiki bar, fitness center, tennis on site. Jetty, boardwalk & walk paths. Excellent location, pets allowed. RRR-00819.2023
Nov. 3 – 10
$531 CAD per night
4.81 out of 5 average rating, 27 reviews

Popular amenities for Longboat Key vacation rentals

Stay near Longboat Key's top sights

IMG Academy36 locals recommend
Beer Can Island32 locals recommend
Dry Dock Waterfront Grill74 locals recommend
Mar Vista Dockside Restaurant88 locals recommend
IMG Academy Golf Club9 locals recommend
New Pass Grill & Bait Shop33 locals recommend

Other great vacation rentals in Longboat Key

Guest favourite
Condo in Longboat Key
Island property on Longboat Key by the Beach
Oct. 16 – 23
$451 CAD per night
4.94 out of 5 average rating, 18 reviews
Guest favourite
Condo in Longboat Key
Best views of the beach from your balcony Unit 301
Aug. 31 – Sep. 7
$471 CAD per night
4.85 out of 5 average rating, 82 reviews
Guest favourite
Condo in Longboat Key
Amazing 2/2 Condo LBK w/ Spectacular Bay Views!
Jul. 26 – Aug. 2
$650 CAD per night
5.0 out of 5 average rating, 7 reviews
Guest favourite
Condo in Longboat Key
Secluded Bayside Gem with beautiful bay views
May 31 – Jun. 7
$473 CAD per night
4.96 out of 5 average rating, 50 reviews
Guest favourite
Townhouse in Longboat Key
Updated Townhome, Secluded Beach + Pool
Jun. 14 – 21
$598 CAD per night
5.0 out of 5 average rating, 24 reviews
Guest favourite
Condo in Longboat Key
Spacious 2 bedroom Longboat Key Condo
Aug. 28 – Sep. 4
$499 CAD per night
4.94 out of 5 average rating, 33 reviews
Superhost
Home in Longboat Key
Zilli Villa, a 2,000 sf home right on the beach.
Nov. 23 – 30
$1,076 CAD per night
5.0 out of 5 average rating, 7 reviews
Superhost
Apartment in Longboat Key
Right on the beach.Renovated ground Floor unit 63.
May 1 – 8
$354 CAD per night
4.85 out of 5 average rating, 55 reviews
Superhost
Condo in Longboat Key
Beach Castle Resort, Pool, TennisWalk to Beach/Bay
Nov. 13 – 20
$424 CAD per night
4.88 out of 5 average rating, 8 reviews
Guest favourite
Home in Anna Maria
ami skyview
Dec. 12 – 19
$1,494 CAD per night
5.0 out of 5 average rating, 27 reviews
Superhost
Home in Sarasota
Mediterranean Estate: Fruit & Botanical Gardens
Sep. 5 – 12
$1,313 CAD per night
5.0 out of 5 average rating, 4 reviews
Guest favourite
Condo in Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
Sep. 8 – 15
$666 CAD per night
4.99 out of 5 average rating, 89 reviews

Quick stats about vacation rentals in Longboat Key

Total rentals

800 properties

Rentals with a pool

610 properties have a pool

Pet-friendly rentals

140 properties allow pets

Family-friendly rentals

580 properties are a good fit for families

Total number of reviews

8.3K reviews

Nightly prices starting at

$41 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key