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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Fleming Key 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, (23 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is ￥21,587
￥68,572 total
includes taxes & fees
Sep 16 - Sep 17
Road's End | Prime Old Town Location! Updated Home w/ Pool
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

2. 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 ￥29,975
￥90,502 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.

3. 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 ￥28,407
￥113,110 total
includes taxes & fees
Sep 23 - Sep 24
Sea Esta Suite | Located On Iconic Duval w/ Pool
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, (8 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
Casa Havana | Old Town Condo w/ Pool & Balcony
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

5. 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.
Private Parking, Heated Pool - Sweet Caroline
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

6. 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 ￥25,528
￥46,715 total
includes taxes & fees
Sep 17 - Sep 18
Poolside Cottage #411
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 ￥25,911
￥46,284 total
includes taxes & fees
Sep 13 - Sep 14
One Bedroom Suite | Beachside Resort
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, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is ￥25,528
￥46,715 total
includes taxes & fees
Sep 16 - Sep 17
Poolside Cottage #412
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, (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 ￥45,199
￥143,959 total
includes taxes & fees
Sep 21 - Sep 22
Southernmost Retreat | On Duval! With Hot Tub, Patio
A backyard with a swimming pool, wooden deck, and a covered patio area.

10. 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 ￥65,608
￥186,469 total
includes taxes & fees
Sep 16 - Sep 17
Conch Cove | Private Oasis with Heated Pool!
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

11. 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 ￥63,917
￥143,758 total
includes taxes & fees
Sep 16 - Sep 17
Passover Cottage | Private Pool & Ideal Key West Location
A swimming pool with a wooden deck, a covered patio area, and a building with large windows and a covered porch.

12. BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (133 reviews)
"Great location to everything in Key West. Exactly as advertised."
United States
Jennifer B.
The price is ￥68,994
￥193,395 total
includes taxes & fees
Sep 14 - Sep 15
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath 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 ￥48,376
￥115,642 total
includes taxes & fees
Sep 14 - Sep 15
Atlantis House Suites
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building in the background.

14. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
The price is ￥45,996
￥93,775 total
includes taxes & fees
Sep 16 - Sep 17
Gone Coastal
A kitchen with white cabinets, a granite countertop, a built-in oven, and a wall-mounted air conditioner.

15. 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 ￥53,662
￥136,608 total
includes taxes & fees
Sep 14 - Sep 15
Coconut Palm - Steps from Duval with Private Pool
A backyard with a swimming pool, a barbecue grill, and a covered patio area.

16. Poolside Paradise - Heated Pool & Steps to Duval St

Poolside Paradise - Heated Pool & Steps to Duval St
Old Town Key West
8.8 out of 10, Excellent, (24 reviews)
"Great location"
United States
Peter S.
Poolside Paradise - Heated Pool & Steps to Duval St
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 ￥45,398
￥92,950 total
includes taxes & fees
Sep 16 - Sep 17
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A modern living room with a white sofa, blue chairs, and a kitchen in the background.

18. Harbor House Penthouse- B

Harbor House Penthouse- B
Key West Historic District
9.8 out of 10, Exceptional, (17 reviews)
"Great location "
United States
Shawn G.
The price is ￥49,850
￥172,509 total
includes taxes & fees
Sep 16 - Sep 17
Harbor House Penthouse- B
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 ￥76,706
￥168,133 total
includes taxes & fees
Sep 15 - Sep 16
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 ￥41,258
￥89,193 total
includes taxes & fees
Sep 22 - Sep 23
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 Fleming Key Hotel Reviews

Southwinds Motel

Southwinds Motel

10/10 Excellent
"SOUTHWINDS MOTEL WAS AN ABSOLUTELY PERFECT TO STAY IN KW!!!! The amenities were perfect, the moring breakfast was just perfect, and thee LOCATION IS SUPER GREAT. Literally minutes from everywhere. WE WILL BE BACK, FOR SURE!!!!!"
Norman 2-night trip
Posted 15 hours ago
Southwinds Motel

Find out more about Fleming Key

Fleming Key Vacation Homes information

Number of reviews
711
Accommodation
798 Vacation Homes
Lowest Price
￥46,284
Highest Price
￥193,395

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