Search Cottages in Longboat Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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 €527
includes taxes & fees
12 Apr - 13 Apr
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
The price is €489
includes taxes & fees
5 Apr - 6 Apr
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 €481
includes taxes & fees
12 Apr - 13 Apr
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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 €296
includes taxes & fees
15 Apr - 16 Apr
7mi to Anna Maria Newly Renovated Private Cottage

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 €188
includes taxes & fees
13 Apr - 14 Apr
The "Grouper"

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 €354
includes taxes & fees
6 Apr - 7 Apr
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 €470
includes taxes & fees
14 Apr - 15 Apr
Steps 2 Beach- Cottage w/king bd +2bikes +parking

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 €746
includes taxes & fees
14 Apr - 15 Apr
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 €409
includes taxes & fees
6 Apr - 7 Apr
Sunny PaG Island rental w/bikes-just steps2beach

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.
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 €302
includes taxes & fees
11 Apr - 12 Apr
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 €344
includes taxes & fees
8 Apr - 9 Apr
Stylish Retro Vibes Private BBQ & Beach Access

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

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

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.
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 traveller
The price is €484
includes taxes & fees
19 Apr - 20 Apr
Casey Key Beachfront Escape: Charming 1BR Cottage

Sarasota Home w/ Heated Pool: 3 Mi to Airport!

Sarasota Home w/ Heated Pool: 3 Mi to Airport!
3.0 star property
Whitfield Estates
Sarasota Home w/ Heated Pool: 3 Mi to Airport!

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

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is €2,662
includes taxes & fees
7 Apr - 8 Apr
3716 7th Ave W

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 €466
includes taxes & fees
7 Apr - 8 Apr
Unwind Poolside + Walk to Beach! Sarasota Retreat

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
659
Accommodation
23 Cottages
Lowest Price
€188
Highest Price
€2,662

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 favourite. 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 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.