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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Cottages in Longboat Key

Our top choices for Longboat Key cottages

The "Grouper"
Beach

The "Grouper"

9.6 out of 10, Exceptional, (31)
"Great location."
$189 nightly
The price is $211
Aug 29 - Aug 30
Total with taxes and fees
The "Grouper"
7mi to Anna Maria Newly Renovated Private Cottage
Private kitchen

7mi to Anna Maria Newly Renovated Private Cottage

$224 nightly
The price is $249
Aug 29 - Aug 30
Total with taxes and fees
7mi to Anna Maria Newly Renovated Private Cottage
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
$450 nightly
The price is $502
Aug 25 - Aug 26
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Sun loungers, beach towels

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (77)
"Its right next to everything we needed"
$272 nightly
The price is $303
Aug 27 - Aug 28
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (95)
"We have stayed at this cottage before- just love this beach."
$386 nightly
The price is $430
Aug 25 - Aug 26
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Romantic Island Getaway Just Steps from the Beach
TV

Romantic Island Getaway Just Steps from the Beach

2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
$342 nightly
The price is $381
Aug 25 - Aug 26
Total with taxes and fees
Romantic Island Getaway Just Steps from the Beach
Sunny PaG Island rental w/bikes-just steps2beach
On the beach

Sunny PaG Island rental w/bikes-just steps2beach

9.0 out of 10, Wonderful, (18)
"Cute little beach house a short walk to the beach, property shared with several other rentals but felt peaceful and quiet. Parking is on street nearby. Convenient location to explore the St. Petersburg area."
$262 nightly
The price is $280
Sep 7 - Sep 8
Total with taxes and fees
Sunny PaG Island rental w/bikes-just steps2beach
Private King Bed Suite-Near AMI Beach-Walk D’Town.
Marina

Private King Bed Suite-Near AMI Beach-Walk D’Town.

9.6 out of 10, Exceptional, (36)
"The Sea Horse Cottage and Bradenton area were charming and beautiful....we had a nice time!!"
$292 nightly
The price is $326
Aug 30 - Aug 31
Total with taxes and fees
Private King Bed Suite-Near AMI Beach-Walk D’Town.
5 star Guest House heated pool on the water!
Beach

5 star Guest House heated pool on the water!

$457 nightly
The price is $509
Aug 25 - Aug 26
Total with taxes and fees
5 star Guest House heated pool on the water!
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A heated pool

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
$406 nightly
The price is $453
Aug 25 - Aug 26
Total with taxes and fees
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Beach

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (32)
"Fun stay, great location"
$220 nightly
The price is $246
Aug 25 - Aug 26
Total with taxes and fees
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Adorable Cottage with Covered Balconies and Private Pool
A heated pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (39)
"This property definitely did not disappoint! Fantastic location that’s close to both the beach and the pier. Shops and food are all within walking distance. The backyard was a hit. The pool and putting green were a fun addition to the large backyard space. Great communication from the hosts who made sure our check in process went well and called to make sure everything was going well and to let them know if we needed anything. Would definitely stay at this space again. "
$489 nightly
The price is $545
Aug 25 - Aug 26
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
Steps to Beach+bikes VaCay getaway on PaG island
On the beach

Steps to Beach+bikes VaCay getaway on PaG island

10.0 out of 10, Exceptional, (12)
"These Bungalows are small, but packed with character and are less than a two minute walk to one of Floridas most serene, beautiful beaches. Owner was very helpful!"
$271 nightly
The price is $291
Aug 26 - Aug 27
Total with taxes and fees
Steps to Beach+bikes VaCay getaway on PaG island
Beautiful Guest House Near the Beach with Private Pool!
A heated pool

Beautiful Guest House Near the Beach with Private Pool!

8.4 out of 10, Very Good, (26)
"The space directly above the local taco and donut shops was exactly as advertised! Clean, quaint, and perfect for our family of 5 that took full advantage of the private pool and 1 block walk to the beach. Can't wait to come back!!"
$446 nightly
The price is $497
Aug 26 - Aug 27
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Fridge, microwave, oven, stovetop

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

$723 nightly
The price is $805
Sep 2 - Sep 3
Total with taxes and fees
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (60)
"We loved this little cottage and will absolutely go back in the future. Thank you so much for a wonderful retreat. "
$409 nightly
The price is $456
Aug 25 - Aug 26
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
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

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

10/10 Excellent
"We had a great stay. Great location and was a very nice place. When checking in, there wasn’t a key for us in the box. But the owner was quick to respond and fix the situation. We would definitely stay again."
Reggie L. 3-night trip
Posted 1 day ago
Beach front 2 bed-2 bath private balcony, modern with Gulf front views