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

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Longboat Key cottages

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.
The price is HK$776
HK$1,670 total
includes taxes & fees
28 Jul - 29 Jul
The "Grouper"
Interior

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is HK$1,372
HK$2,634 total
includes taxes & fees
28 Jul - 29 Jul
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (200 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is HK$2,501
HK$3,261 total
includes taxes & fees
22 Jul - 23 Jul
The Inn On Siesta Key
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.
The price is HK$670
HK$2,127 total
includes taxes & fees
26 Jul - 27 Jul
Coastal Luxury 7mi to Anna Maria Private Cottage
Outdoor dining

Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is HK$690
HK$2,628 total
includes taxes & fees
26 Jul - 27 Jul
Cozy Lido Key Studio Steps to Beach & Kayaking
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is HK$1,323
HK$5,282 total
includes taxes & fees
30 Jul - 31 Jul
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, (127 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is HK$2,391
HK$5,133 total
includes taxes & fees
22 Jul - 23 Jul
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
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 HK$1,323
HK$5,282 total
includes taxes & fees
30 Jul - 31 Jul
Yellow Palm Cottage steps from the beach
Exterior

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (47 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is HK$2,352
HK$7,770 total
includes taxes & fees
19 Aug - 20 Aug
Adorable Cottage with Covered Balconies and Private Pool
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
The price is HK$2,092
HK$3,819 total
includes taxes & fees
15 Aug - 16 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"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
Front of property

Pool, Dock & Kayaks: Waterfront Palmetto Home

Pool, Dock & Kayaks: Waterfront Palmetto Home
3.0 star property
Palmetto
10.0 out of 10, Exceptional, (1 review)
"This house was absolutely stunning. The kitchen is fully loaded with double appliances. The pool is warm, clean, and salt water! The view is stunning. The area is safe and quiet. We walked 20 min to hit up a cute coffee shop, paddled the kayaks, and took Uber to the Moat Marine and Planetarium. Great for a family. Better if you have a car. "
United States
Carley
Pool, Dock & Kayaks: Waterfront Palmetto Home
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is HK$18,503
HK$24,192 total
includes taxes & fees
24 Jul - 25 Jul
3716 7th Ave W
Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
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.
Cabana Cottage Across street from Beach and Heated Pool
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)
The price is HK$776
HK$2,361 total
includes taxes & fees
2 Aug - 3 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
On the beach, sun-loungers, beach towels

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (128 reviews)
"Fantastic property and exactly as described. Can’t beat being right on the beach!"
United States
Alina K.
The price is HK$1,552
HK$3,686 total
includes taxes & fees
22 Jul - 23 Jul
Casey Key Beachfront Escape: Charming 1BR Cottage
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.
The price is HK$1,826
HK$3,752 total
includes taxes & fees
22 Jul - 23 Jul
Steps 2 Beach- Cottage w/king bd +2bikes +parking
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, (25 reviews)
"Great location! "
United States
Quinton W.
The price is HK$1,104
HK$2,687 total
includes taxes & fees
3 Aug - 4 Aug
Sunny PaG Island rental w/bikes-just steps2beach
Exterior

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

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
10.0 out of 10, Exceptional, (28 reviews)
"All as promised…clean, bright…small but perfect for a couple at the beach. "
United States
reva g.
The price is HK$1,054
HK$2,607 total
includes taxes & fees
20 Aug - 21 Aug
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (80 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 HK$1,944
HK$4,416 total
includes taxes & fees
9 Aug - 10 Aug
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.
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Top Longboat Key Hotel Reviews

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

8/10 Good
"Beautiful gulf views and excellent beach access!! When we weren’t on the beach, we enjoyed the wonderful views from the balcony!!!"
Jacob O. 3-night trip
Posted 8 hours ago
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
205
Accommodation
24 Cottages
Lowest Price
HK$2,634
Highest Price
HK$24,192

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.

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