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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Cottages in Longboat Key

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, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
$227 nightly
The price is $257
Nov 11 - Nov 12
Total with taxes and fees
The Inn On Siesta Key
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, (2)
"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.
$246 nightly
The price is $274
Nov 11 - Nov 12
Total with taxes and fees
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

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

Casey Key
9.2 out of 10, Wonderful, (68)
"We so enjoy this little property loved the beach and it’s coziness would definitely refer ones to it and would stay again found lots of shells and sharks teeth"
United States
Bobbie H.
$518 nightly
The price is $577
Nov 15 - Nov 16
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Exterior
The "Grouper"

The "Grouper"

Sunny Shores
9.2 out of 10, Wonderful, (41)
"Very clean and nice place ."
United States
Sherry S.
$191 nightly
The price is $213
Nov 12 - Nov 13
Total with taxes and fees
The "Grouper"
Exterior
Steps to Beach+bikes VaCay getaway on PaG island

Steps to Beach+bikes VaCay getaway on PaG island

Pass-a-Grille
9.8 out of 10, Exceptional, (19)
"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.
$244 nightly
The price is $260
Nov 12 - Nov 13
Total with taxes and fees
Steps to Beach+bikes VaCay getaway on PaG island
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key
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.
$305 nightly
The price is $305
Nov 11 - Nov 12
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Terrace/patio
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)
"The location was perfect with close beach access and surrounded by a lot of fun businesses. We loved being over the pizza shop, could go down there and grab food or drinks! We enjoyed our stay very much!"
United States
Sarah E.
$463 nightly
The price is $517
Nov 14 - Nov 15
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
Outdoor dining
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

2.0 star property
Nokomis
$150 nightly
The price is $166
Nov 17 - Nov 18
Total with taxes and fees
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
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, (176)
"clean, nice amenities and great location"
United States
Robert K.
$344 nightly
The price is $384
Nov 11 - Nov 12
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Palmetto
$222 nightly
The price is $247
Nov 17 - Nov 18
Total with taxes and fees
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
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)
"Wonderful stay. Everything was perfect. The location can’t be beat, 2 minute walk to a beautiful beach. 2nd visit and we’ll be back!"
United States
Valerie W.
$246 nightly
The price is $263
Nov 18 - Nov 19
Total with taxes and fees
Sunny PaG Island rental w/bikes-just steps2beach
Terrace/patio
Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

Siesta Key
10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
$548 nightly
The price is $597
Nov 11 - Nov 12
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool
Exterior
Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach

2.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (3)
"Although there are laundry facilities on property, the area is kept locked and this unit is not permitted access. We were unable to do any laundry unless we traveled two miles to Holmes Beach to the Laundromat. This property IS very quiet. The trolley stops are literally at the end of the driveway, but there are no shops or businesses within close walking distance. Also, there were beach chairs and towels, but THERE ARE NO EXTRAS here, which is unlike any other Vrbo/AirBnb we have visited. There...
United States
Amy
$333 nightly
The price is $371
Nov 11 - Nov 12
Total with taxes and fees
Romantic Island Getaway! Just Steps from the Beach
Outdoor dining
Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!

Anna Maria
8.6 out of 10, Excellent, (29)
"The house is above 2 restaurants. But that did not cause us problems. There had been a huge storm on day of arrival and the pool got trashed. I called and had someone out next morning. There was an annoying fire beeping alarming going off everyday and that really didn't get addressed during our stay despite my calls. I had to shut it off multiple times. Overall it was a great stay. Beds so comfortable I miss them! Plenty of room for us ladies. Would consider coming back if the alarm was...
United States
Dawn H.
$435 nightly
The price is $485
Nov 16 - Nov 17
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
Terrace/patio
5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!

South Sarasota
$455 nightly
The price is $507
Nov 11 - Nov 12
Total with taxes and fees
5 star Guest House heated pool on the water!
Outdoor dining
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

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

Casey Key
9.4 out of 10, Exceptional, (104)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
$409 nightly
The price is $456
Nov 12 - Nov 13
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Exterior
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Pass-a-Grille
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.
$319 nightly
The price is $342
Dec 4 - Dec 5
Total with taxes and fees
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Pool
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)
"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.
$472 nightly
The price is $525
Nov 19 - Nov 20
Total with taxes and fees
Nest Cottage Across street from beach and Heated Pool
Terrace/patio
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)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
$473 nightly
The price is $527
Nov 18 - Nov 19
Total with taxes and fees
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

Right on the beach.Renovated ground Floor unit 63.

Right on the beach.Renovated ground Floor unit 63.

10/10 Excellent
"Host was exceptional and all vacation needs were met"
Andrea C. 6-night trip
Posted 5 days ago
Right on the beach.Renovated ground Floor unit 63.

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
606
Accommodation
23 Cottages
Lowest Price
$166
Highest Price
$597

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.

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