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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, (195 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
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 ¥39,598
¥83,609 total
includes taxes & fees
Mar 31 - Apr 1
Direct Beachfront 2BR Cottage on Casey Key!

Steps to Riverwalk! Dtwn Bradenton Snowbird Haven

Steps to Riverwalk! Dtwn Bradenton Snowbird Haven
3.0 star property
Bradenton
The price is ¥18,649
¥79,000 total
includes taxes & fees
Mar 30 - Mar 31
Steps to Riverwalk! Dtwn Bradenton Snowbird Haven

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

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
The price is ¥8,773
¥75,861 total
includes taxes & fees
Mar 30 - Mar 31
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)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
The price is ¥53,649
¥91,216 total
includes taxes & fees
Apr 12 - Apr 13
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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.
Beautiful Condo on Pine Ave, 2 Blocks to Beach

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 ¥18,681
¥49,521 total
includes taxes & fees
Mar 31 - Apr 1
7mi to Anna Maria Newly Renovated Private Cottage

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, (46 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 ¥42,151
¥82,352 total
includes taxes & fees
Apr 14 - Apr 15
Steps 2 Beach- Cottage w/king bd +2bikes +parking

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (55 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 ¥15,780
¥33,627 total
includes taxes & fees
Apr 1 - Apr 2
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, (35 reviews)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
The price is ¥58,656
¥160,340 total
includes taxes & fees
Apr 15 - Apr 16
Beautiful Guest House Near the Beach with Private Pool!

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 ¥43,523
¥76,928 total
includes taxes & fees
Apr 19 - Apr 20
Sunny PaG Island rental w/bikes-just steps2beach

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, (123 reviews)
"The property was amazing, great fishing spots around, the host was great and very responsive with our hiccup in dates. Thank you for being flexible and switched dates for us, we had a great time"
United States
Yoandra B.
The price is ¥70,929
¥132,262 total
includes taxes & fees
Apr 12 - Apr 13
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Beach Gear Provided! Omas House in Bradenton!

Beach Gear Provided! Omas House in Bradenton!
3.0 star property
Bradenton
The price is ¥31,240
¥83,754 total
includes taxes & fees
Mar 30 - Mar 31
Beach Gear Provided! Omas House in Bradenton!

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ¥366,597
¥490,546 total
includes taxes & fees
Apr 11 - Apr 12
3716 7th Ave W

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.8 out of 10, Excellent, (3 reviews)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
The price is ¥44,629
¥115,065 total
includes taxes & fees
Apr 1 - Apr 2
Romantic Island Getaway! Just Steps from the Beach

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 ¥27,096
¥57,755 total
includes taxes & fees
Apr 14 - Apr 15
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (115 reviews)
"Excellent Host, Great location, Excited to return"
United States
Anonymous traveler
The price is ¥39,598
¥81,598 total
includes taxes & fees
Mar 29 - Mar 30
Casey Key Beachfront Escape: Charming 1BR Cottage

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 ¥19,959
¥51,646 total
includes taxes & fees
Apr 14 - Apr 15
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (36 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is ¥26,299
¥41,911 total
includes taxes & fees
Mar 30 - Mar 31
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

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

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely place to stay. The four of us were SO comfortable. The place was clean and beautiful. Very well maintained. You can tell by the high quality finishes that this is someone’s home and they maintain it as such. There was an unforeseen circumstance that popped up with the island doing some work that affected the house while we were there. I messaged the owner and within minutes he had replied and had all the necessary people on the way to fix it. They fixed it all while we were at...
United States
Devon F.
The price is ¥102,297
¥206,408 total
includes taxes & fees
Apr 27 - Apr 28
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
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
961
Accommodation
17 Cottages
Lowest Price
¥33,627
Highest Price
¥490,546

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.