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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Longboat Key and around

Our top choices for Longboat Key cottages

The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The price is €258
includes taxes & fees
21 Aug - 22 Aug
The Inn On Siesta Key
The "Grouper"
Beach

The "Grouper"

9.6 out of 10, Exceptional, (31)
"Great location."
The price is €185
includes taxes & fees
20 Sept - 21 Sept
The "Grouper"
Romantic Island Getaway Just Steps from the Beach
TV

Romantic Island Getaway Just Steps from the Beach

2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
The price is €449
includes taxes & fees
21 Aug - 22 Aug
Romantic Island Getaway Just Steps from the Beach
7mi to Anna Maria Newly Renovated Private Cottage
Private kitchen

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Sun-loungers, beach towels

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (76)
"Its right next to everything we needed"
The price is €267
includes taxes & fees
27 Aug - 28 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
The price is €448
includes taxes & fees
24 Aug - 25 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun-loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (95)
"We have stayed at this cottage before- just love this beach."
The price is €454
includes taxes & fees
20 Sept - 21 Sept
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Beach

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

9.8 out of 10, Exceptional, (32)
"Fun stay, great location"
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Private King Bed Suite-Near AMI Beach-Walk D’Town.
Marina

Private King Bed Suite-Near AMI Beach-Walk D’Town.

9.6 out of 10, Exceptional, (36)
"The Sea Horse Cottage and Bradenton area were charming and beautiful....we had a nice time!!"
Private King Bed Suite-Near AMI Beach-Walk D’Town.
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A heated pool

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
Beautiful Condo on Pine Ave, 2 Blocks to Beach
5 star Guest House heated pool on the water!
Beach

5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!
Nest Cottage Across street from beach and Heated Pool
Pool

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."
The price is €369
includes taxes & fees
23 Aug - 24 Aug
Nest Cottage Across street from beach and Heated Pool
Adorable Cottage with Covered Balconies and Private Pool
A heated pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (39)
"This property definitely did not disappoint! Fantastic location that’s close to both the beach and the pier. Shops and food are all within walking distance. The backyard was a hit. The pool and putting green were a fun addition to the large backyard space. Great communication from the hosts who made sure our check in process went well and called to make sure everything was going well and to let them know if we needed anything. Would definitely stay at this space again. "
Adorable Cottage with Covered Balconies and Private Pool
Sunny PaG Island rental w/bikes-just steps2beach
On the beach

Sunny PaG Island rental w/bikes-just steps2beach

9.0 out of 10, Wonderful, (18)
"Cute little beach house a short walk to the beach, property shared with several other rentals but felt peaceful and quiet. Parking is on street nearby. Convenient location to explore the St. Petersburg area."
Sunny PaG Island rental w/bikes-just steps2beach
Beautiful Guest House Near the Beach with Private Pool!
A heated pool

Beautiful Guest House Near the Beach with Private Pool!

8.4 out of 10, Very good, (26)
"The space directly above the local taco and donut shops was exactly as advertised! Clean, quaint, and perfect for our family of 5 that took full advantage of the private pool and 1 block walk to the beach. Can't wait to come back!!"
Beautiful Guest House Near the Beach with Private Pool!
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun-loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (60)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is €401
includes taxes & fees
24 Aug - 25 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
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

Longboat Key beach house - 5 min walk to the beaches and top local restaurants

Longboat Key beach house - 5 min walk to the beaches and top local restaurants

10/10 Excellent
"Great experience woukd definitely do it again!."
Matt D. 2-night trip
Posted 2 days ago
Longboat Key beach house - 5 min walk to the beaches and top local restaurants

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.