Photo by throwingsofas

Search Longboat Key Cottages

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Jan 9 - Jan 11
In two weeks
Jan 16 - Jan 18
In one month
Jan 30 - Feb 1
In two months
Feb 27 - Mar 1

Our top choices for Longboat Key cottages

The Lookout, 1 King Bedroom 1 Bath | Terrace/patio
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (192)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

Cottage in Bradenton

7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (3)
"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.
$249 nightly
The price is $277
Jan 4 - Jan 5
Total with taxes and fees
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota

Cottage in Bayou Oaks

Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota
2.0 star property
$97 nightly
The price is $107
Feb 1 - Feb 2
Total with taxes and fees
Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota
Exterior
Direct Beachfront 2BR Cottage on Casey Key!

Cottage in Casey Key

Direct Beachfront 2BR Cottage on Casey Key!
9.2 out of 10, Wonderful, (69)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
$430 nightly
The price is $479
Jan 4 - Jan 5
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
Exterior
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cottage in South Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (81)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
$265 nightly
The price is $296
Jan 12 - Jan 13
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Cottage in Sarasota

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (177)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
United States
Alexis
$426 nightly
The price is $475
Jan 19 - Jan 20
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Terrace/patio
Adorable Cottage with Covered Balconies and Private Pool

Cottage in Anna Maria

Adorable Cottage with Covered Balconies and Private Pool
9.6 out of 10, Exceptional, (41)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
United States
C. S.
$856 nightly
The price is $955
Jan 22 - Jan 23
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Cottage in Sarasota

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
$299 nightly
The price is $333
Jan 6 - Jan 7
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Cottage in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
$277 nightly
The price is $277
Jan 4 - Jan 5
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Steps to Beach+bikes VaCay getaway on PaG island

Cottage in Pass-a-Grille

Steps to Beach+bikes VaCay getaway on PaG island
9.8 out of 10, Exceptional, (20)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
$304 nightly
The price is $338
Jan 6 - Jan 7
Total with taxes and fees
Steps to Beach+bikes VaCay getaway on PaG island
Property grounds
Nest Cottage Across street from beach and Heated Pool

Cottage in Siesta Key

Nest Cottage Across street from beach and Heated Pool
10.0 out of 10, Exceptional, (2)
"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
Exterior
Blue Dolphin Cottage steps from the beach

Cottage in Siesta Key Village

Blue Dolphin Cottage steps from the beach
$567 nightly
The price is $610
Jan 6 - Jan 7
Total with taxes and fees
Blue Dolphin Cottage steps from the beach
Exterior
Yellow Palm Cottage steps from the beach

Cottage in Siesta Key Village

Yellow Palm Cottage steps from the beach
$556 nightly
The price is $598
Jan 6 - Jan 7
Total with taxes and fees
Yellow Palm Cottage steps from the beach
Terrace/patio
5 star Guest House heated pool on the water!

Cottage in South Sarasota

5 star Guest House heated pool on the water!
$437 nightly
The price is $489
Jan 4 - Jan 5
Total with taxes and fees
5 star Guest House heated pool on the water!
Exterior
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

Cottage in Anna Maria

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
10.0 out of 10, Exceptional, (1)
"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.
$796 nightly
The price is $888
Jan 6 - Jan 7
Total with taxes and fees
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Outdoor dining
Beautiful Guest House Near the Beach with Private Pool!

Cottage in Anna Maria

Beautiful Guest House Near the Beach with Private Pool!
8.8 out of 10, Excellent, (31)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
$783 nightly
The price is $874
Jan 15 - Jan 16
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
Outdoor dining
Casey Key Beachfront Escape: Charming 1BR Cottage

Cottage in Casey Key

Casey Key Beachfront Escape: Charming 1BR Cottage
9.4 out of 10, Exceptional, (109)
"A true hidden gem on a great stretch of beach. Loved my time there and would recommend it. "
United States
John V.
$384 nightly
The price is $431
Jan 5 - Jan 6
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
Exterior
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Cottage in Pass-a-Grille

Steps 2 Beach-Island Cottage w/king bd+2bike+parking
9.8 out of 10, Exceptional, (41)
"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.
$421 nightly
The price is $472
Jan 10 - Jan 11
Total with taxes and fees
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
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
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

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

10/10 Excellent
"Incredible place. Already booked again!! "
Julie T. 5-night trip
Posted 3 days ago
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
639
Accommodation
23 Cottages
Lowest Price
$277
Highest Price
$955

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.

Explore a world of travel with Expedia