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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Longboat Key cottages

Interior

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
The price is £484
includes taxes & fees
22 Feb - 23 Feb
Stylish Retro Vibes Private BBQ & Beach Access
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The price is £442
includes taxes & fees
16 Feb - 17 Feb
The Inn On Siesta Key
Exterior

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
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 £297
includes taxes & fees
9 Mar - 10 Mar
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Property grounds

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (3 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.
The price is £255
includes taxes & fees
28 Feb - 1 Mar
7mi to Anna Maria Newly Renovated Private Cottage
House (3 Bedrooms) | Interior

3 Mi to Downtown Bradenton: Family Home w/ Yard!

3 Mi to Downtown Bradenton: Family Home w/ Yard!
3.0 star property
Bradenton
The price is £351
includes taxes & fees
8 Feb - 9 Feb
3 Mi to Downtown Bradenton: Family Home w/ Yard!
Terrace/patio

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (112 reviews)
"Simple old-school beach shack - so hard to find these days, absolutely loved it. Right on the water, best location along Nokomis Beach/Casey Key...short walk to restaurants also....absolutely fantastic."
United States
HAYLEY S.
The price is £329
includes taxes & fees
9 Feb - 10 Feb
Casey Key Beachfront Escape: Charming 1BR Cottage
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (45 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is £161
includes taxes & fees
8 Feb - 9 Feb
The "Grouper"
Exterior

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
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 £749
includes taxes & fees
21 Feb - 22 Feb
Yellow Palm Cottage steps from the beach
Exterior

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (20 reviews)
"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.
The price is £265
includes taxes & fees
9 Feb - 10 Feb
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Exterior

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, (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 £355
includes taxes & fees
9 Feb - 10 Feb
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Interior

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 £388
includes taxes & fees
10 Feb - 11 Feb
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
Exterior

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
Bayou Oaks
The price is £100
includes taxes & fees
12 Feb - 13 Feb
1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
Property grounds

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, (18 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is £224
includes taxes & fees
10 Feb - 11 Feb
Sunny PaG Island rental w/bikes-just steps2beach
Exterior

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.6 out of 10, Exceptional, (41 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 £637
includes taxes & fees
12 Feb - 13 Feb
Adorable Cottage with Covered Balconies and Private Pool
Property grounds

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, (122 reviews)
"Great location"
United States
Steve H.
The price is £517
includes taxes & fees
8 Mar - 9 Mar
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Interior

Moon Dreams Cottage 1.7 mi to Nokomis Beach

Moon Dreams Cottage 1.7 mi to Nokomis Beach
Nokomis
The price is £288
includes taxes & fees
24 Feb - 25 Feb
Moon Dreams Cottage 1.7 mi to Nokomis Beach
Exterior

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
Exterior

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, (32 reviews)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
The price is £611
includes taxes & fees
9 Feb - 10 Feb
Beautiful Guest House Near the Beach with Private Pool!
Exterior

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, (44 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 £494
includes taxes & fees
9 Mar - 10 Mar
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Property grounds

Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
"It was a beautiful place. Great staff. Awesome experience."
United States
Nicholas M.
The price is £621
includes taxes & fees
16 Feb - 17 Feb
Haven cottage Across street from beach and Heated Pool
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

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand

10/10 Excellent
"Welcome material was clear and helpful. Access was easy. All amenities were as expected. Location was superb, very quiet and peaceful for us as a couple. Thoroughly enjoyed our stay, right on the beach."
Philip S. 2-night trip
Posted 2 days ago
Beachfront Bliss on Longboat Key- Steps to the sand

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
684
Accommodation
23 Cottages
Lowest Price
£161
Highest Price
£749

Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Get comfortable at Queen's Gate Resort, a 2.5-star cottage not far from downtown. Amenities here include a nearby beach and a barbecue grill. Another family-friendly pick where you can swap the concrete jungle for fresh air and nature 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. Longboat Key has no shortage of family-friendly attractions to check out that'll entertain the kids. Florida Maritime Museum at Cortez and Island Gallery West promise a fun day out for visitors of all ages.
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.

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