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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Longboat Key cottages

The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (194 reviews)
"Great place to stay! "
United States
Carlos
The price is AED 1,537
AED 1,965 total
includes taxes & fees
3 Mar - 4 Mar
The Inn On Siesta Key
Terrace/patio

Cottage in Casey Key

Casey Key Beachfront Escape: Charming 1BR Cottage
9.4 out of 10, Exceptional, (112 reviews)
"Great location for a quick beach getaway!"
United States
Thomas D.
The price is AED 1,462
AED 2,496 total
includes taxes & fees
3 Mar - 4 Mar
Casey Key Beachfront Escape: Charming 1BR Cottage
House (2 Bedrooms) | Front of property

Cottage in Bradenton

Steps to Riverwalk! Dtwn Bradenton Snowbird Haven
3.0 star property
The price is AED 665
AED 2,086 total
includes taxes & fees
2 Mar - 3 Mar
Steps to Riverwalk! Dtwn Bradenton Snowbird Haven
Exterior

Cottage in Sarasota

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (178 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 AED 1,462
AED 2,392 total
includes taxes & fees
4 Mar - 5 Mar
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

Cottage in Pass-a-Grille

Steps 2 Beach- Cottage w/king bd +2bikes +parking
9.8 out of 10, Exceptional, (45 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 AED 1,739
AED 2,850 total
includes taxes & fees
9 Mar - 10 Mar
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Exterior

Cottage in Siesta Key Village

Yellow Palm Cottage steps from the beach
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 AED 1,145
AED 3,030 total
includes taxes & fees
2 Mar - 3 Mar
Yellow Palm Cottage steps from the beach
Exterior

Cottage in Siesta Key Village

Blue Dolphin Cottage steps from the beach
The price is AED 1,087
AED 2,929 total
includes taxes & fees
2 Mar - 3 Mar
Blue Dolphin Cottage steps from the beach
Interior

Cottage in Sarasota

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
The price is AED 454
AED 1,604 total
includes taxes & fees
9 Mar - 10 Mar
Stylish Retro Vibes Private BBQ & Beach Access
Exterior

Cottage in Sunny Shores

The "Grouper"
9.4 out of 10, Exceptional, (48 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is AED 364
AED 775 total
includes taxes & fees
4 Mar - 5 Mar
The "Grouper"
Property grounds

Cottage in Anna Maria

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
9.6 out of 10, Exceptional, (123 reviews)
"Great place and great location........"
United States
chris w.
The price is AED 1,319
AED 2,651 total
includes taxes & fees
12 Mar - 13 Mar
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

Cottage in Anna Maria

Beautiful Condo on Pine Ave, 2 Blocks to Beach
8.8 out of 10, Excellent, (25 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 AED 2,564
AED 5,415 total
includes taxes & fees
21 Mar - 22 Mar
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Property grounds

Cottage in Bradenton

7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (4 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.
7mi to Anna Maria Newly Renovated Private Cottage
House (4 Bedrooms) | Interior

Cottage in Bradenton

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
The price is AED 738
AED 2,459 total
includes taxes & fees
24 Mar - 25 Mar
Outdoor Kitchen & Gaming Garage: Bradenton Retreat
Exterior

Cottage in Sarasota

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
10.0 out of 10, Exceptional, (1 review)
"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 AED 562
AED 1,268 total
includes taxes & fees
9 Mar - 10 Mar
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Property grounds

Cottage in Siesta Key Village

Pink Mango Cottage steps from the beach
The price is AED 1,355
AED 3,298 total
includes taxes & fees
6 Mar - 7 Mar
Pink Mango Cottage steps from the beach
Terrace/patio

Cottage in Siesta Key

Cabana Cottage Across street from Beach and Heated Pool
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 AED 1,688
AED 4,366 total
includes taxes & fees
3 Mar - 4 Mar
Cabana Cottage Across street from Beach and Heated Pool
Property grounds

Cottage in Siesta Key

Haven cottage Across street from beach and Heated Pool
9.8 out of 10, Exceptional, (7 reviews)
"It was a beautiful place. Great staff. Awesome experience."
United States
Nicholas M.
The price is AED 1,713
AED 2,881 total
includes taxes & fees
3 Mar - 4 Mar
Haven cottage Across street from beach and Heated Pool
Interior

Cottage in Fruitville

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
The price is AED 1,078
AED 2,738 total
includes taxes & fees
15 Mar - 16 Mar
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
Exterior

Cottage in Anna Maria

Adorable Cottage with Covered Balconies and Private Pool
9.6 out of 10, Exceptional, (42 reviews)
"The house was fantastic, clean and a great location. It had Everything and more than you needed. Will definitely return for a longer trip x"
United Kingdom
Danielle E.
The price is AED 1,616
AED 4,357 total
includes taxes & fees
5 Mar - 6 Mar
Adorable Cottage with Covered Balconies and Private Pool
Terrace/patio

Cottage in Casey Key

Direct Beachfront 2BR Cottage on Casey Key!
9.2 out of 10, Wonderful, (70 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 AED 1,829
AED 3,134 total
includes taxes & fees
8 Mar - 9 Mar
Direct Beachfront 2BR Cottage on Casey Key!
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.
View all properties

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA

10/10 Excellent
"This is a lovely spot on a quiet beach. We really enjoyed our trip. "
Jennifer B. 7-night trip
Posted 3 days ago
Oceanfront Oasis – Longboat Key 226 by RVA

Frequently asked questions

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.