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

Key West Vacation Rentals

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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 vacation homes

A building with a red door, a covered porch, and a bamboo plant in the foreground.

1. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (24 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is CA $197
CA $630 total
includes taxes & fees
Sep 29 - Sep 30
Road's End | Prime Old Town Location! Updated Home w/ Pool
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

2. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"We stayed here for our honeymoon and it was perfect. The place was clean and well appointed. The pool right outside was huge and we spent lots of time there. Highly recommend!"
United States
DeAnna Z.
The price is CA $234
CA $428 total
includes taxes & fees
Sep 25 - Sep 26
Poolside Cottage #411
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

3. Casa Havana | Old Town Condo w/ Pool & Balcony

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is CA $258
CA $866 total
includes taxes & fees
Sep 25 - Sep 26
Casa Havana | Old Town Condo w/ Pool & Balcony
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

4. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is CA $274
CA $836 total
includes taxes & fees
Sep 28 - Sep 29
Luxury two floor apartment in prime location of famous Duval Street
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

5. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is CA $259
CA $1,047 total
includes taxes & fees
Sep 23 - Sep 24
Sea Esta Suite | Located On Iconic Duval w/ Pool
A patio area with a fountain, seating, and umbrellas.

6. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (4 reviews)
"Great little place 1 block off Duval. A nice quiet oasis from everything a street away. Moon Dog restaurant is around the block and was great for breakfast and dinner. Great kitchen! The mattress upstairs could use a firmer replacement IMHO…overall very good spot!"
United States
Robert J.
The price is CA $197
CA $630 total
includes taxes & fees
Sep 29 - Sep 30
Andros Suite | Perfect Location with Pool!
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

7. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is CA $297
CA $732 total
includes taxes & fees
Sep 23 - Sep 24
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A wooden deck with a large tree, outdoor seating, and a marina in the background.

8. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is CA $260
CA $437 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Cottage #412
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

9. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (7 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is CA $208
CA $389 total
includes taxes & fees
Sep 29 - Sep 30
One Bedroom Suite | Beachside Resort
A porch with wicker furniture and a white railing.

10. Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
Old Town Key West
8.8 out of 10, Excellent, (19 reviews)
"Great location!"
United States
Kayla S.
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
A patio area with wicker furniture and a grill.

11. Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.6 out of 10, Exceptional, (33 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
United States
Drew L.
The price is CA $412
CA $1,329 total
includes taxes & fees
Sep 29 - Sep 30
Southernmost Retreat | On Duval! With Hot Tub, Patio
A kitchen with white cabinets, a granite countertop, a built-in oven, and a wall-mounted air conditioner.

12. Coconut Palm - Steps from Duval with Private Pool

Coconut Palm - Steps from Duval with Private Pool
Old Town Key West
9.0 out of 10, Wonderful, (39 reviews)
"Great Property Excellent location "
United States
Jim B.
The price is CA $491
CA $1,281 total
includes taxes & fees
Sep 23 - Sep 24
Coconut Palm - Steps from Duval with Private Pool
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

13. Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
United States
Aaron J.
The price is CA $443
CA $1,065 total
includes taxes & fees
Sep 23 - Sep 24
Atlantis House Suites
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

14. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (32 reviews)
"Amazing home and location! So close to Duval and all the fun places. I highly recommend staying here. Very comfy, clean and convenient."
United States
Susana C.
The price is CA $420
CA $1,021 total
includes taxes & fees
Oct 5 - Oct 6
Private Parking, Heated Pool - Sweet Caroline
A backyard with a swimming pool, wooden deck, and a covered patio area.

15. Conch Cove | Private Oasis with Heated Pool!

Conch Cove | Private Oasis with Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is CA $597
CA $1,709 total
includes taxes & fees
Sep 29 - Sep 30
Conch Cove | Private Oasis with Heated Pool!
A covered patio with a glass table and chairs, a pool, and a wooden deck.

16. Casa De Cubana | New! Cuban-Style Home Near Duval

Casa De Cubana | New! Cuban-Style Home Near Duval
Old Town Key West
10.0 out of 10, Exceptional, (41 reviews)
"This was a beutiful location and stay. "
United States
Jon-Paul G.
The price is CA $597
CA $1,613 total
includes taxes & fees
Sep 29 - Sep 30
Casa De Cubana | New! Cuban-Style Home Near Duval
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

17. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (7 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is CA $379
CA $765 total
includes taxes & fees
Oct 6 - Oct 7
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

18. Passover Cottage | Private Pool & Ideal Key West Location

Passover Cottage | Private Pool & Ideal Key West Location
Old Town Key West
10.0 out of 10, Exceptional, (19 reviews)
"We had the most amazing stay the house was perfect very clean lots of room big pool and large outdoor space and GREAT location. We will definitely return."
United States
Jennifer Y.
The price is CA $583
CA $1,321 total
includes taxes & fees
Sep 25 - Sep 26
Passover Cottage | Private Pool & Ideal Key West Location
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

19. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
10.0 out of 10, Exceptional, (38 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is CA $722
CA $1,615 total
includes taxes & fees
Sep 29 - Sep 30
Keys Breeze - Walk to Duval, Private Pool
A clear swimming pool with lounge chairs and palm trees.

20. Another Day in Paradise

Another Day in Paradise
Stock Island
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for what we were looking for"
United States
Megan A.
The price is CA $376
CA $832 total
includes taxes & fees
Oct 4 - Oct 5
Another Day in Paradise
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

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Overall an excellent stay. Pool is somewhat small but nice. Staff is overall top notch. Location is about as good as you can get if your plan is to hang in Old Town. Would definitely recommend."
David 5-night trip
Posted 3 hours ago
La Concha Key West, Autograph Collection

Find out more about Key West

Key West Vacation Homes information

Number of reviews
717
Accommodation
916 Vacation Homes
Lowest Price
CA $389
Highest Price
CA $1,709

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