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Our top choices for Longboat Key cottages

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 ¥47,263
¥95,975 total
includes taxes & fees
Apr 23 - Apr 24
Direct Beachfront 2BR Cottage on Casey Key!

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
Family Fun: Ping Pong, Bbq, Walk to Park Nearby

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, (181 reviews)
"Very close to the village and we only had to cross the road to access the beach!! Loved it!!"
United States
Kim H.
The price is ¥61,061
¥100,814 total
includes taxes & fees
Apr 8 - Apr 9
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Lanai & Pond at Tranquil Bradenton Retreat!

Lanai & Pond at Tranquil Bradenton Retreat!
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"I really enjoyed how easy it was to get to the location, and how clean and spacious it was. Although it was a short visit to help my daughter move out of college, it provided a great place to relax after the busy move. The environment was very peaceful and safe."
United States
Ching-Wei Tabitha
The price is ¥17,229
¥64,656 total
includes taxes & fees
Apr 6 - Apr 7
Lanai & Pond at Tranquil Bradenton Retreat!

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, (47 reviews)
"Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)"
United States
James C.
The price is ¥47,878
¥86,941 total
includes taxes & fees
Apr 28 - Apr 29
Steps 2 Beach- Cottage w/king bd +2bikes +parking

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (4 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 ¥16,511
¥46,726 total
includes taxes & fees
Apr 26 - Apr 27
7mi to Anna Maria Newly Renovated Private Cottage

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, (19 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is ¥37,845
¥68,789 total
includes taxes & fees
Apr 6 - Apr 7
Sunny PaG Island rental w/bikes-just steps2beach

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (56 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 ¥15,701
¥33,459 total
includes taxes & fees
Apr 27 - Apr 28
The "Grouper"

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, (36 reviews)
"I couldnt have booked a better spot for my kids. I was nervous it being above a restaurant but you couldnt even tell. It was so tranquil in the backyard and upstairs, during the day we took the golf cart to the beach or shopped around and this was the most convenient place I ever stayed at. It was decorated better than most people decorate their own homes I just loved it and so did my kids and their friends. Cleanliness was perfect, decor, location, I couldnt have asked for anything better,...
United States
Danielle
The price is ¥40,521
¥135,425 total
includes taxes & fees
Apr 14 - Apr 15
Beautiful Guest House Near the Beach with Private Pool!

Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (1 review)
"This is a great location for a beach getaway. It is steps from Sarasota Bay, very close to shopping, restaurants, and entertainment, and a short walk to the beach. The home is beautifully decorated and gives those beachy vibes. It is a very comfortable place to relax after a day in the sun. There is plenty of outdoor space, as well. The host has provided 2 bikes and that is an excellent way to travel the Island.Rex was easy to work with and very responsive to all our needs. We can’t wait to...
United States
Diane C.
Bridge Street Beach House | Wi-Fi | Center of All

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.8 out of 10, Excellent, (3 reviews)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is ¥24,408
¥55,060 total
includes taxes & fees
Apr 11 - Apr 12
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
The price is ¥13,640
¥62,489 total
includes taxes & fees
Apr 8 - Apr 9
Stylish Retro Vibes Private BBQ & Beach Access

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, (1 review)
"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.
The price is ¥125,869
¥228,147 total
includes taxes & fees
Apr 30 - May 1
Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

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 ¥29,194
¥85,896 total
includes taxes & fees
Apr 7 - Apr 8
Unwind Poolside + Walk to Beach! Sarasota Retreat

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.6 out of 10, Exceptional, (45 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 ¥54,240
¥160,406 total
includes taxes & fees
May 1 - May 2
Adorable Cottage with Covered Balconies and Private Pool

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (86 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ¥15,701
¥46,005 total
includes taxes & fees
Apr 28 - Apr 29
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (117 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveler
The price is ¥44,091
¥87,855 total
includes taxes & fees
Apr 19 - Apr 20
Casey Key Beachfront Escape: Charming 1BR Cottage

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, (4 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.
The price is ¥19,144
¥32,034 total
includes taxes & fees
May 3 - May 4
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ¥364,780
¥488,114 total
includes taxes & fees
Apr 7 - Apr 8
3716 7th Ave W

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is ¥193,222
¥285,144 total
includes taxes & fees
Apr 7 - Apr 8
Siesta Heron 7
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
671
Accommodation
17 Cottages
Lowest Price
¥32,034
Highest Price
¥488,114

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.