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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Key West vacation homes

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

1. 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, (56 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 $1,045 total
includes taxes & fees
Oct 29 - Oct 30
Sea Esta Suite | Located On Iconic Duval w/ Pool
A wooden deck with a large tree, outdoor seating, and a marina in the background.

2. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is CA $233
CA $429 total
includes taxes & fees
Oct 25 - Oct 26
Poolside Cottage #412
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

3. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
The price is CA $233
CA $430 total
includes taxes & fees
Oct 29 - Oct 30
Poolside Cottage #411
A patio area with a fountain, seating, and umbrellas.

4. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (5 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 $631 total
includes taxes & fees
Nov 2 - Nov 3
Andros Suite | Perfect Location with Pool!
A building with a red door, a covered porch, and a bamboo plant in the foreground.

5. 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
9.6 out of 10, Exceptional, (27 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
United States
BARBARA Y.
The price is CA $311
CA $790 total
includes taxes & fees
Nov 15 - Nov 16
Road's End | Prime Old Town Location! Updated Home w/ Pool
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

6. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (9 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is CA $238
CA $427 total
includes taxes & fees
Oct 25 - Oct 26
One Bedroom Suite | Beachside Resort
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

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

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is CA $351
CA $1,158 total
includes taxes & fees
Nov 22 - Nov 23
Casa Havana | Old Town Condo w/ Pool & Balcony
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

8. 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 $413
CA $999 total
includes taxes & fees
Nov 17 - Nov 18
Luxury two floor apartment in prime location of famous Duval Street
A patio area with wicker furniture and a grill.

9. 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, (34 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 $413
CA $1,330 total
includes taxes & fees
Oct 30 - Oct 31
Southernmost Retreat | On Duval! With Hot Tub, Patio
A clear swimming pool with lounge chairs and palm trees.

10. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is CA $352
CA $802 total
includes taxes & fees
Oct 26 - Oct 27
Slice of Paradise
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

11. 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, (137 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is CA $378
CA $834 total
includes taxes & fees
Oct 26 - Oct 27
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

12. 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, (8 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 $378
CA $834 total
includes taxes & fees
Oct 28 - Oct 29
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

13. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (33 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 $602
CA $1,252 total
includes taxes & fees
Oct 27 - Oct 28
Private Parking, Heated Pool - Sweet Caroline
A pool with lounge chairs, a covered barbecue area, and a building with a patio.

14. 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 $602
CA $1,399 total
includes taxes & fees
Nov 17 - Nov 18
Coconut Palm - Steps from Duval with Private Pool
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, (43 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is CA $598
CA $1,711 total
includes taxes & fees
Oct 25 - Oct 26
Conch Cove | Private Oasis with Heated Pool!
A covered outdoor patio with a pool, seating area, and lush greenery.

16. Coconut Palm by Brightwild Island Home w Pool

Coconut Palm by Brightwild Island Home w Pool
2.0 star property
Old Town Key West
The price is CA $772
CA $1,522 total
includes taxes & fees
Nov 17 - Nov 18
Coconut Palm by Brightwild Island Home w Pool
A balcony with white railings, palm trees, and a view of a street with parked cars and buildings.

17. Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Old Town Key West
9.4 out of 10, Exceptional, (56 reviews)
"Great location and we would stay here again. "
United States
Brandon A.
The price is CA $560
CA $1,399 total
includes taxes & fees
Nov 8 - Nov 9
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
A clear swimming pool with lounge chairs and palm trees in the background.

18. Poolside Paradise

Poolside Paradise
Stock Island
The price is CA $415
CA $919 total
includes taxes & fees
Oct 30 - Oct 31
Poolside Paradise
A pool with a white deck, surrounded by lush greenery and a white fence.

19. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is CA $973
CA $1,935 total
includes taxes & fees
Oct 27 - Oct 28
Keys Breeze - Walk to Duval, Private Pool
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

20. 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, (21 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 $582
CA $1,318 total
includes taxes & fees
Oct 30 - Oct 31
Passover Cottage | Private Pool & Ideal Key West Location
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

8/10 Good
"Checkin was ok, staff were ok. Room was ok . Main bathroom sink was blocked and ensuite door was broken/off the tracks. Said they would look at it. Directly across the road from the beach. Free shuttle to and from Old Town. Very basic hotel for the price"
Belinda 1-night trip
Posted 4 hours ago
Margaritaville Beach House Key West

Find out more about Key West

Key West Vacation Homes information

Number of reviews
617
Accommodation
932 Vacation Homes
Lowest Price
CA $427
Highest Price
CA $1,935

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