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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Longboat Key cottages

Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
$302 nightly
The price is $342
Jun 3 - Jun 4
Total with taxes and fees
The Inn On Siesta Key
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (73 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
$485 nightly
The price is $541
May 26 - May 27
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
Exterior

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
$709 nightly
The price is $768
May 25 - May 26
Total with taxes and fees
Yellow Palm Cottage steps from the beach
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (66 reviews)
"Perfect location to Anna Maria Island-real “old Florida” feel."
United States
Mary W.
$190 nightly
The price is $212
May 25 - May 26
Total with taxes and fees
The "Grouper"
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
$709 nightly
The price is $768
May 25 - May 26
Total with taxes and fees
Pink Mango Cottage steps from the beach
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$557 nightly
The price is $621
Jun 12 - Jun 13
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
$236 nightly
The price is $263
May 26 - May 27
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage
Property grounds

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Palmetto
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
$212 nightly
The price is $237
Jun 9 - Jun 10
Total with taxes and fees
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Property grounds

Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
$641 nightly
The price is $715
May 25 - May 26
Total with taxes and fees
Haven cottage Across street from beach and Heated Pool
Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
$364 nightly
The price is $364
May 25 - May 26
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Property grounds

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
$637 nightly
The price is $710
May 25 - May 26
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Exterior

Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.8 out of 10, Exceptional, (48 reviews)
"Yes, the Host went over the top very clean very accommodating great location!!!"
United States
Susan T.
$475 nightly
The price is $530
Jun 9 - Jun 10
Total with taxes and fees
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,731 nightly
The price is $3,086
Jun 2 - Jun 3
Total with taxes and fees
3716 7th Ave W
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
$321 nightly
The price is $358
May 31 - Jun 1
Total with taxes and fees
Lido Key Getaway - Bikes & Beach Gear
Property grounds

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.0 out of 10, Wonderful, (20 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
$326 nightly
The price is $363
May 29 - May 30
Total with taxes and fees
Sunny PaG Island rental w/bikes-just steps2beach
Exterior

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
10.0 out of 10, Exceptional, (25 reviews)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
$346 nightly
The price is $386
May 25 - May 26
Total with taxes and fees
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (38 reviews)
"Fun stay, great location"
United States
Theresa H.
$228 nightly
The price is $254
May 25 - May 26
Total with taxes and fees
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Exterior

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (47 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
$1,166 nightly
The price is $1,299
Jun 14 - Jun 15
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
Exterior

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"Everything was fantastic!"
United States
Kevin O.
$1,113 nightly
The price is $1,242
Jun 13 - Jun 14
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
Outdoor dining

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (5 reviews)
"The property was very well stocked, had a bowl for our dog an very clean! It was the petfect place for our visit with local family. The "Florida Room" was lovely and the view was excellent. Very peaceful location."
United States
Marie W.
$179 nightly
The price is $199
May 28 - May 29
Total with taxes and fees
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
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 the room was amazing. The entire property was very clean and well kept."
Jane B. 3-night trip
Posted 1 day ago
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
889
Accommodation
23 Cottages
Lowest Price
$199
Highest Price
$3,086

Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Put your feet up at Queen's Gate Resort, a 2.5-star cottage just a short drive from downtown. Conveniences here include a nearby beach and WiFi. Another family-friendly option where you can swap the concrete jungle for wide open spaces is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a guest favorite. After checking in and chilling in your comfortable new digs, it's time to head out and start exploring. Coquina Beach and Cortez Beach are among the best family-friendly attractions in Longboat Key.
Why book your cottage in Longboat Key with Expedia?
Booking a cottage in Longboat Key is as easy as deciding on your travel dates and selecting your ideal place for outdoor recreation and relaxation. From high-end retreats to affordable properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveler tastes. As for the best deals around? We've got them too!
How can I find cheap cottages in Longboat Key?
Expedia is here to help you track down cheap cottages in Longboat Key. To find a fantastic stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.

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