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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Key West vacation homes

A wooden deck with a large tree, outdoor seating, and a marina in the background.

1. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Definitely would stay here again. Very smooth process. Property was perfect for our family of 5. We loved having access to the pool right at our doorstep. Very accurate photos and description. Excellent value for the money."
United States
Danielle D.
The price is SAR 625
SAR 1,144 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #412
A patio area with a fountain, seating, and umbrellas.

2. 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 SAR 529
SAR 1,683 total
includes taxes & fees
13 Oct - 14 Oct
Andros Suite | Perfect Location with Pool!
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 SAR 625
SAR 1,102 total
includes taxes & fees
14 Oct - 15 Oct
Poolside Cottage #411
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

4. 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, (10 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is SAR 694
SAR 2,318 total
includes taxes & fees
12 Oct - 13 Oct
Casa Havana | Old Town Condo w/ Pool & Balcony
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, (54 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is SAR 842
SAR 2,995 total
includes taxes & fees
29 Oct - 30 Oct
Sea Esta Suite | Located On Iconic Duval w/ Pool
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

6. 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 SAR 732
SAR 2,229 total
includes taxes & fees
13 Oct - 14 Oct
Luxury two floor apartment in prime location of famous Duval Street
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

7. 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 SAR 634
SAR 1,126 total
includes taxes & fees
11 Oct - 12 Oct
One Bedroom Suite | Beachside Resort
A porch with wicker furniture and a white railing.

8. 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 clear swimming pool with lounge chairs and palm trees.

9. 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 SAR 1,014
SAR 2,210 total
includes taxes & fees
11 Oct - 12 Oct
Slice of Paradise
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

10. 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 SAR 794
SAR 1,952 total
includes taxes & fees
13 Oct - 14 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
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, (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 SAR 1,107
SAR 3,525 total
includes taxes & fees
11 Oct - 12 Oct
Southernmost Retreat | On Duval! With Hot Tub, Patio
A pool area with a tiled deck, a wooden fence, and a staircase leading to a covered porch.

12. Sweet Caroline by Brightwild Pool Parking

Sweet Caroline by Brightwild Pool Parking
2.0 star property
Key West Historic District
The price is SAR 1,385
SAR 2,928 total
includes taxes & fees
14 Oct - 15 Oct
Sweet Caroline by Brightwild Pool Parking
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 SAR 1,185
SAR 2,843 total
includes taxes & fees
12 Oct - 13 Oct
Atlantis House Suites
A backyard with a swimming pool, lounge chairs, and a wooden fence.

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 SAR 1,479
SAR 3,583 total
includes taxes & fees
14 Oct - 15 Oct
Coconut Palm - Steps from Duval with Private Pool
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

15. 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 SAR 1,179
SAR 2,769 total
includes taxes & fees
14 Oct - 15 Oct
Private Parking, Heated Pool - Sweet Caroline
A hallway with closed louvered doors, a wall-mounted light fixture, and a framed tropical-themed artwork.

16. Duval Vibes • Pool • 10 Guests

Duval Vibes • Pool • 10 Guests
Old Town Key West
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and tidy, had trouble opening the door and the host was there to help with answering the questions I had. Super fun place to stay or even to relax"
United States
Grace K.
The price is SAR 1,633
SAR 3,246 total
includes taxes & fees
13 Oct - 14 Oct
Duval Vibes • Pool • 10 Guests
A backyard with a swimming pool, wooden deck, and a covered patio area.

17. Conch Cove | Private Oasis with Heated Pool!

Conch Cove | Private Oasis with Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is SAR 1,602
SAR 4,516 total
includes taxes & fees
26 Oct - 27 Oct
Conch Cove | Private Oasis with Heated Pool!
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

18. 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 SAR 1,014
SAR 2,229 total
includes taxes & fees
18 Oct - 19 Oct
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A living room with a door, a window with blinds, a lamp, a sofa with patterned cushions, and a small table.

19. The Mesa House - One block from Duval St

The Mesa House - One block from Duval St
Key West Historic District
9.8 out of 10, Exceptional, (9 reviews)
"Perfect home for our family! The location was ideal for exploring Key West and enjoying the nightlife on Duval. The beds were comfortable and the kitchen had everything we needed. We will return!"
United States
Debbie P.
The price is SAR 2,208
SAR 5,152 total
includes taxes & fees
14 Oct - 15 Oct
The Mesa House - One block from Duval St
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, (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 SAR 1,561
SAR 3,492 total
includes taxes & fees
14 Oct - 15 Oct
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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"The staff the management at the front desk"
Sherrie 1-night trip
Posted 9 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection