A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Key West cottages

Interior

1. Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (7 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is AED 929
AED 2,083 total
includes taxes & fees
12 Aug - 13 Aug
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Exterior

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (362 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is AED 331
AED 888 total
includes taxes & fees
1 Sep - 2 Sep
Old Wooden Bridge Resort and Marina
Property grounds

3. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (32 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is AED 857
AED 1,728 total
includes taxes & fees
11 Aug - 12 Aug
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Outdoor dining

4. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"The bedrooms and bathrooms were a little small but everything else was fantastic. We loved the outdoor spaces."
United States
Carla R.
The price is AED 1,047
AED 1,945 total
includes taxes & fees
11 Aug - 12 Aug
Canal front, dockage, 2 bedroom, 2 bath
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 Key West Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"The pool was great. The staff was amazing and the location was only minutes from everything. We rented a car which was ideal. We thoroughly enjoyed our vacation and will go back again!"
Kyle 7-night trip
Posted 1 hour ago
Hyatt Vacation Club at Windward Pointe, Key West

Frequently asked questions

How much do cottages in Key West cost?
Cottages in Key West range between AED 888 and AED 2,083 per night. These retreats offer a chance to touch base with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Key West?
Select from multiple cottages in Key West with a total average guest review rating of 9.1. Simonton Court Cottages is an ideal place to rest your feet between adventures. This 3.5-star cottage also comes with a garden and a nearby beach. Casa Manana Key West Monthly: 2 Br is another leading option with visitors in this area. It has a 3-star rating and amenities including a king-sized bed and a swimming pool.
How many cottages are there in Key West?
Stay in touch with nature in one of the 116 cottages waiting for you in Key West. To help you choose an ideal property, make use of our handy filters to search for must-have perks or amenities.
Why book your cottage in Key West with Expedia?
We think a getaway should be simple, so if you're seeking cottages in Key West at the perfect price, Expedia has you covered. Keep the budget in check and check in to a cheap option far from the hustle and bustle, or splurge on a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Key West?
A good way to spot cheap cottages in Key West is with Expedia's handy filter tool. Tailor your search results by amenities, star rating and budget to land unbeatable deals in a couple of clicks.