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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Key West cottages

A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

1. OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (63 reviews)
"We had such a great time on our visit. The place was exactly like the only photos and we enjoyed the pool, the area and the other visiters. Beautiful Old Town feel!"
United States
Debra S.
OSPREY STUDIO @ The Colony-Sleeps up to 4
A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

2. Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (84 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
$480 nightly
The price is $526
Sep 29 - Sep 30
Total with taxes and fees
Get your ISLAND STLYE on!
A patio with a grill, yellow chairs, and a table under a blue umbrella, surrounded by a wooden deck and a lattice fence.

3. HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
$480 nightly
The price is $526
Sep 30 - Oct 1
Total with taxes and fees
HIDDEN OASIS 3 blocks from Duval
A two-story building with balconies, surrounded by lush greenery and palm trees.

4. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (35 reviews)
"The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again"
United States
Pauline B.
$637 nightly
The price is $712
Oct 3 - Oct 4
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

5. Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Great location, clean and well equipped."
United States
Richard M.
$550 nightly
The price is $605
Sep 30 - Oct 1
Total with taxes and fees
Find your zen at HIDDEN TREASURE
A floating houseboat with a covered deck and seating area, docked at a marina.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Nice place"
United States
abhimanyu
$225 nightly
The price is $253
Sep 27 - Sep 28
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A balcony with a view of the sea and a distant shoreline.

7. 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, (33 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.
$435 nightly
The price is $467
Oct 2 - Oct 3
Total with taxes and fees
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
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

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"It was a great family experience"
mark 5-night trip
Posted less than an hour ago
Hampton Inn Key West FL

Find out more about Key West

Key West Cottages information

Number of reviews
628
Accommodation
110 Cottages
Lowest Price
$253
Highest Price
$712

Frequently asked questions

How much do cottages in Key West cost?
Cottages in Key West range between $253 and $712 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 9.5. 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 110 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.
Are there any family-friendly cottages in Key West?
A trip with the family in Key West is simple at Casa Manana Key West Monthly: 2 Br. With amenities including a king-sized bed and a barbecue grill, you'll find all the comforts of home at this 3-star cottage. Simonton Court Cottages is another family-friendly stay where you and your squad can escape the hustle and bustle of city life. This cottage has a 3-star rating and amenities including housekeeping services and WiFi. Key West boasts plenty of family-friendly attractions to check out that'll entertain the kids. Smathers Beach and South Beach promise a fun day out for both young and old.
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.
What is there to do in Key West near my cottage?
Key West has enough experiences and activities to keep you amused for weeks, starting with Nancy Forrester's Secret Garden. Donkey Milk House, Clarence S. Higgs Memorial Beach Park and Duval Street are other wonderful attractions. If you have more time, Smathers Beach and Mallory Square will add the finishing touches to your itinerary.

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