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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, (199 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 £398
includes taxes & fees
12 Jul - 13 Jul
The Inn On Siesta Key

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (9 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
The price is £191
includes taxes & fees
24 Jun - 25 Jun
Coastal Luxury 7mi to Anna Maria Private Cottage

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (75 reviews)
"It was perfect. We had a great time."
United States
Karen M.
The price is £410
includes taxes & fees
23 Jun - 24 Jun
Direct Beachfront 2BR Cottage on Casey Key!

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is £251
includes taxes & fees
25 Jun - 26 Jun
Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (71 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is £163
includes taxes & fees
26 Jun - 27 Jun
The "Grouper"

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is £457
includes taxes & fees
24 Jun - 25 Jun
Pink Mango Cottage steps from the beach

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.
The price is £479
includes taxes & fees
30 Jun - 1 Jul
Yellow Palm Cottage steps from the beach

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, (184 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is £491
includes taxes & fees
3 Jul - 4 Jul
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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.
The price is £857
includes taxes & fees
2 Jul - 3 Jul
Adorable Cottage with Covered Balconies and Private Pool

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
Nest Cottage Across street from beach and Heated Pool

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, (126 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is £562
includes taxes & fees
23 Jun - 24 Jun
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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.
The price is £946
includes taxes & fees
6 Jul - 7 Jul
Cabana Cottage Across street from Beach and Heated Pool

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
The price is £327
includes taxes & fees
30 Jun - 1 Jul
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

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)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
The price is £876
includes taxes & fees
17 Jul - 18 Jul
Beautiful Guest House Near the Beach with Private Pool!

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, (27 reviews)
"Nice place, a little noisy in the morning but a good convenient location for a girls trip. It was clean and beds were decent. The water pressure was not great but that being said, I would stay here again!"
United States
Amy H.
The price is £803
includes taxes & fees
27 Jun - 28 Jun
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"This was our family’s first time visiting AMI and we will definitely be back. The location of the property was awesome - its steps from the beach. It’s less than a mile to walk to restaurants and shops, but we loved having a golf cart that made it easy to go out for dinners and get groceries from the Publix. I was a little nervous with what I read about the Bean Point beach because of the currents, but my 4, 6, and 8 year olds were totally fine in the water. The beach was clean and is great for...
United States
Tierney L.
Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is £2,202
includes taxes & fees
3 Jul - 4 Jul
3716 7th Ave W

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)
"Lowkey, quiet, clean, amenities to cook, great host and great view. Happy to go back again."
United States
Bryan S.
The price is £141
includes taxes & fees
28 Jun - 29 Jun
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

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
The price is £461
includes taxes & fees
12 Jul - 13 Jul
Unwind Poolside + Walk to Beach! Sarasota Retreat

Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.

Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.
Bradenton Beach
9.6 out of 10, Exceptional, (13 reviews)
"It is a nice place. The furnitures in the bathroom and the bedrooms a little old but overall is a nice little place. "
United States
kelly n.
The price is £302
includes taxes & fees
28 Jun - 29 Jun
Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.
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

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Longboat Key Cottages information

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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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