A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Search Longboat Key Cottages

  • 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

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Longboat Key cottages

Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
$474 nightly
The price is $535
Jul 18 - Jul 19
Total with taxes and fees
The Inn On Siesta Key
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$190 nightly
The price is $212
Jul 15 - Jul 16
Total with taxes and fees
The "Grouper"
House (2 Bedrooms) | Interior

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
$297 nightly
The price is $336
Jul 13 - Jul 14
Total with taxes and fees
Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (78 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
$490 nightly
The price is $548
Jul 13 - Jul 14
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
$600 nightly
The price is $646
Jul 15 - Jul 16
Total with taxes and fees
Pink Mango Cottage steps from the beach
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, (126 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
$592 nightly
The price is $660
Jul 13 - Jul 14
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.2 out of 10, Wonderful, (23 reviews)
"Great location! "
United States
Quinton W.
$336 nightly
The price is $375
Aug 2 - Aug 3
Total with taxes and fees
Sunny PaG Island rental w/bikes-just steps2beach
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (10 reviews)
"Very nice location. "
United States
Daniel o.
$229 nightly
The price is $255
Jul 13 - Jul 14
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage
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, (187 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$469 nightly
The price is $522
Jul 19 - Jul 20
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Outdoor dining

Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
$313 nightly
The price is $349
Jul 15 - Jul 16
Total with taxes and fees
Cozy Lido Key Studio Steps to Beach & Kayaking
Exterior

Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (49 reviews)
"Yes, the Host went over the top very clean very accommodating great location!!!"
United States
Susan T.
$529 nightly
The price is $590
Jul 22 - Jul 23
Total with taxes and fees
Steps 2 Beach- Cottage w/king bd +2bikes +parking
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, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
$956 nightly
The price is $1,067
Jul 17 - Jul 18
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
Outdoor dining

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Anna Maria
10.0 out of 10, Exceptional, (3 reviews)
"This was our family’s first time visiting AMI and we will definitely be back. The location of the property was awesome - its steps from the beach. It’s less than a mile to walk to restaurants and shops, but we loved having a golf cart that made it easy to go out for dinners and get groceries from the Publix. I was a little nervous with what I read about the Bean Point beach because of the currents, but my 4, 6, and 8 year olds were totally fine in the water. The beach was clean and is great for...
United States
Tierney L.
$1,280 nightly
The price is $1,426
Jul 15 - Jul 16
Total with taxes and fees
Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,636 nightly
The price is $2,979
Jul 20 - Jul 21
Total with taxes and fees
3716 7th Ave W
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
$320 nightly
The price is $356
Aug 9 - Aug 10
Total with taxes and fees
Cozy Lido Key Bungalow by Pool & Beach
Dining

Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
$724 nightly
The price is $806
Jul 18 - Jul 19
Total with taxes and fees
Lookout Cottage Across street from Beach and Heated Pool
Property grounds

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
$506 nightly
The price is $564
Jul 13 - Jul 14
Total with taxes and fees
Romantic Island Getaway! Just Steps from the Beach
Exterior

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, (89 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
$270 nightly
The price is $301
Aug 2 - Aug 3
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
House (3 Bedrooms) | Interior

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
$541 nightly
The price is $611
Aug 5 - Aug 6
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat
Exterior

Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.

Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.
Bradenton Beach
9.6 out of 10, Exceptional, (15 reviews)
"It is a nice place. The furnitures in the bathroom and the bedrooms a little old but overall is a nice little place. "
United States
kelly n.
$369 nightly
The price is $411
Jul 24 - Jul 25
Total with taxes and fees
Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.
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

Zota Beach Resort

Zota Beach Resort

8/10 Good
"I like it because it was compact and less crowded"
Romik 4-night trip
Posted 14 hours ago
Zota Beach Resort

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
747
Accommodation
23 Cottages
Lowest Price
$212
Highest Price
$2,979

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