Holiday rentals in Longboat Key

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Top-rated holiday 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
$703 SGD per night
4.86 out of 5 average rating, 103 reviews
Guest favourite
Flat in Longboat Key
Ocean Front Studio Special From $99/night
This complex is a 2 story bldg with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures are taken from the condo, so what you see is what you get, direct beautiful Ocean views. Sip your beverage of choice as you enjoy the sunsets and the balmy breezes on your large walkout private patio with a table, chairs, chaise lounges which faces the aqua waters of the Gulf of Mexico. This is a condo that you will want to return to year after year.
11–18 May
$246 SGD per night
4.82 out of 5 average rating, 124 reviews
Guest favourite
Apartment in Longboat Key
The Beach Condo Unit #107 Beachfront
Unit #107 has a private beach access, This end condo unit is quiet, ground floor and only steps to the white sand beach down a private path. . Note that this is a small studio, 330 sq. ft. with queen murphy bed and a queen sofa bed. It has no separate bedroom. Full view of gulf and sunsets. There are only 15 units in the complex, few people on beach or at the heated pool. No daily maid service. Only initial limited supply of products/soaps/towels. Common use W/D across from unit.
3–10 Oct
$253 SGD per night
4.86 out of 5 average rating, 154 reviews

Popular amenities for Longboat Key holiday 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 holiday rentals in Longboat Key

Guest favourite
Townhouse in Longboat Key
Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse
3–10 Nov
$387 SGD per night
4.81 out of 5 average rating, 27 reviews
Guest favourite
Apartment in Longboat Key
Island property on Longboat Key by the Beach
6–13 Oct
$335 SGD per night
4.94 out of 5 average rating, 18 reviews
Guest favourite
Home in Longboat Key
Beautiful Beach House
20–27 Aug
$414 SGD per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Apartment in Longboat Key
Best views of the beach from your balcony Unit 301
31 Aug – 7 Sep
$353 SGD per night
4.85 out of 5 average rating, 82 reviews
Guest favourite
Apartment in Longboat Key
Amazing 2/2 Condo LBK w/ Spectacular Bay Views!
26 Jul – 2 Aug
$461 SGD per night
5.0 out of 5 average rating, 7 reviews
Guest favourite
Townhouse in Longboat Key
Updated Townhome, Secluded Beach + Pool
14–21 Jun
$402 SGD per night
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Longboat Key
Zilli Villa, a 2,000 sf home right on the beach.
23–30 Nov
$807 SGD per night
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Sarasota
Mediterranean Estate: Fruit & Botanical Gardens
5–12 Sep
$954 SGD per night
5.0 out of 5 average rating, 6 reviews
Guest favourite
Guest suite in Sarasota
Mid-Century Modern Beach Getaway
19–26 Oct
$133 SGD per night
4.98 out of 5 average rating, 99 reviews
Guest favourite
Apartment in Bradenton Beach
AMI Perfect Experience
23–30 Nov
$187 SGD per night
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cottage in Osprey
Mattie’s Cottage by the Bay
5–12 Jun
$115 SGD per night
4.94 out of 5 average rating, 17 reviews
Guest favourite
Apartment in Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
8–15 Sep
$487 SGD per night
4.99 out of 5 average rating, 89 reviews

Quick stats about holiday 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

$40 SGD before taxes and fees

Destinations to explore

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