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Holiday Homes in Fleming Key

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Check prices for these dates

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

Our top choices for Fleming Key holiday 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 €394
includes taxes & fees
26 Sept - 27 Sept
Road's End | Prime Old Town Location! Updated Home w/ Pool
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

2. 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.
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.

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.
Casa Havana | Old Town Condo w/ Pool & Balcony
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, (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 €400
includes taxes & fees
27 Sept - 28 Sept
Andros Suite | Perfect Location with Pool!
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

5. 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 €521
includes taxes & fees
28 Sept - 29 Sept
Luxury two floor apartment in prime location of famous Duval Street
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 €262
includes taxes & fees
25 Sept - 26 Sept
Poolside Cottage #411
A porch with wicker furniture and a white railing.

7. 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 swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

8. 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 €247
includes taxes & fees
23 Sept - 24 Sept
One Bedroom Suite | Beachside Resort
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 €824
includes taxes & fees
23 Sept - 24 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio
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 €459
includes taxes & fees
23 Sept - 24 Sept
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

11. 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 €643
includes taxes & fees
5 Oct - 6 Oct
Private Parking, Heated Pool - Sweet Caroline
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.
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 €658
includes taxes & fees
23 Sept - 24 Sept
Atlantis House Suites
A wooden deck with a large tree, outdoor seating, and a marina in the background.

14. 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 €276
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #412
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

15. 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 €816
includes taxes & fees
24 Sept - 25 Sept
Passover Cottage | Private Pool & Ideal Key West Location
A backyard with a swimming pool, wooden deck, and a covered patio area.

16. 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 €1,078
includes taxes & fees
29 Sept - 30 Sept
Conch Cove | Private Oasis with Heated Pool!
A covered patio with a glass table and chairs, a pool, and a wooden deck.

17. 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 €1,031
includes taxes & fees
23 Sept - 24 Sept
Casa De Cubana | New! Cuban-Style Home Near Duval
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 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 €2,002
includes taxes & fees
20 Oct - 21 Oct
Keys Breeze - Walk to Duval, Private Pool
A modern living room with a white sofa, blue chairs, and a kitchen in the background.

19. Harbor House Penthouse- B

Harbor House Penthouse- B
Key West Historic District
9.8 out of 10, Exceptional, (18 reviews)
"Great location "
United States
Shawn G.
Harbor House Penthouse- B
A modern kitchen with white cabinetry, a large island with stools, a built-in oven, and a stainless steel refrigerator.

20. Luxurious Island Pearl-Private Pool - 2BD/2Bath

Luxurious Island Pearl-Private Pool - 2BD/2Bath
Key West Historic District
10.0 out of 10, Exceptional, (60 reviews)
"Excellent property and location!"
United States
Mark B.
Luxurious Island Pearl-Private Pool - 2BD/2Bath
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

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 6 hours ago
La Concha Key West, Autograph Collection

Find out more about Fleming Key

Fleming Key Holiday Homes information

Number of reviews
784
Accommodation
801 Holiday Homes
Lowest Price
€247
Highest Price
€2,002

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