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Our top choices for Longboat Key cottages

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
The price is £306
includes taxes & fees
9 May - 10 May
The Inn On Siesta Key

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is £403
includes taxes & fees
12 May - 13 May
Direct Beachfront 2BR Cottage on Casey Key!

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)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is £210
includes taxes & fees
12 May - 13 May
Coastal Luxury 7mi to Anna Maria Private Cottage

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
The price is £346
includes taxes & fees
10 May - 11 May
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
cortez
10.0 out of 10, Exceptional, (104 reviews)
"The host was always available! The cottage is adorable and homey. Wonderful location and had everything you need for a fun experience."
United States
Janice C.
The price is £213
includes taxes & fees
19 May - 20 May
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (65 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
The price is £159
includes taxes & fees
16 May - 17 May
The "Grouper"

Outdoor Kitchen & Gaming Garage: Bradenton Retreat

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Bradenton
The price is £492
includes taxes & fees
21 May - 22 May
Outdoor Kitchen & Gaming Garage: Bradenton Retreat

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, (23 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.
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

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.
The price is £479
includes taxes & fees
10 May - 11 May
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is £297
includes taxes & fees
31 May - 1 Jun
Lido Key Getaway - Bikes & Beach Gear

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (26 reviews)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is £707
includes taxes & fees
16 May - 17 May
Beautiful Condo on Pine Ave, 2 Blocks to Beach

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.
The price is £259
includes taxes & fees
3 Jun - 4 Jun
Sunny PaG Island rental w/bikes-just steps2beach

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.
The price is £603
includes taxes & fees
21 May - 22 May
Beautiful Guest House Near the Beach with Private Pool!

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is £2,182
includes taxes & fees
10 May - 11 May
3716 7th Ave W

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
Cabana Cottage Across street from Beach and Heated Pool

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.
The price is £177
includes taxes & fees
19 May - 20 May
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
Unwind Poolside + Walk to Beach! Sarasota Retreat

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
Nook Cottage Across street from beach and Heated Pool

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (46 reviews)
"Everything was wonderful. We would love to stay there again. Great location, lots of room, and very comfy beds. "
United States
Jennifer B.
The price is £833
includes taxes & fees
9 May - 10 May
Adorable Cottage with Covered Balconies and Private Pool
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

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
916
Accommodation
23 Cottages
Lowest Price
£159
Highest Price
£2,182

Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Get comfortable at Queen's Gate Resort, a 2.5-star cottage not far from downtown. Amenities here include a nearby beach and a barbecue grill. Another family-friendly pick where you can swap the concrete jungle for fresh air and nature is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a guest favourite. Longboat Key has no shortage of family-friendly attractions to check out that'll entertain the kids. Florida Maritime Museum at Cortez and Island Gallery West promise a fun day out for visitors of all ages.
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 traveller 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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