Default HTG hotel image

Holiday Homes in Fleming Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Fleming Key holiday 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)
"Wonderful stay. Thank you."
United States
shannon b.
The price is AU$416
includes taxes & fees
9 Nov - 10 Nov
Poolside Cottage #412
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

2. 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 AU$1,016
includes taxes & fees
16 Nov - 17 Nov
Casa Havana | Old Town Condo w/ Pool & Balcony
A building with a red door, a covered porch, and a bamboo plant in the foreground.

3. 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, (28 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 AU$617
includes taxes & fees
15 Nov - 16 Nov
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.

4. 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, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is AU$1,034
includes taxes & fees
4 Nov - 5 Nov
Sea Esta Suite | Located On Iconic Duval w/ Pool
A patio area with a fountain, seating, and umbrellas.

5. 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 AU$599
includes taxes & fees
2 Nov - 3 Nov
Andros Suite | Perfect Location with Pool!
A living room with a beige sofa, a white coffee table with a plant, and a view through glass doors to an outdoor area.

6. Waterlane House at Lunara Bay

Waterlane House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
United States
Justin S.
The price is AU$2,028
includes taxes & fees
8 Nov - 9 Nov
Waterlane House at Lunara Bay
Property Overview

7. Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (43 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is AU$2,253
includes taxes & fees
9 Nov - 10 Nov
Suncoast House at Lunara Bay
A swimming pool with a curved edge, surrounded by palm trees and lounge chairs.

8. Poolside Paradise

Poolside Paradise
Stock Island
The price is AU$863
includes taxes & fees
9 Nov - 10 Nov
Poolside Paradise
Living Area

9. Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
The price is AU$2,028
includes taxes & fees
2 Nov - 3 Nov
Capmar House at Lunara Bay
A white building with a porch, surrounded by tropical plants and a pathway leading to the entrance.

10. Shared Pool & Parking - The Cottage at James House

Shared Pool & Parking - The Cottage at James House
Key West Historic District
8.6 out of 10, Excellent, (10 reviews)
"Awesome location! "
United States
Lindsey M.
The price is AU$1,146
includes taxes & fees
14 Nov - 15 Nov
Shared Pool & Parking - The Cottage at James House
Pool Deck with Lounge Chairs

11. The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Great property, terrific hosts - amazing location!"
United States
Jason T.
The price is AU$2,028
includes taxes & fees
2 Nov - 3 Nov
The Seagate Estate at Lunara Bay
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

12. 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, (104 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is AU$1,003
includes taxes & fees
16 Nov - 17 Nov
Luxury two floor apartment in prime location of famous Duval Street
A modern kitchen with a central island, pendant lighting, and wooden chairs.

13. Altair House at Lunara Bay

Altair House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (15 reviews)
"host was very kind to let us do early check-in and late check out. The house is great, was very clean, everything was working perfectly."
United States
Esteban M.
Altair House at Lunara Bay
A wooden deck with a hanging hammock and a view of a green landscape.

14. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is AU$947
includes taxes & fees
30 Nov - 1 Dec
Starlight Serenity - Hideaway with Stunning Views
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

15. 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)
"We had an awesome stay! We enjoyed being able to use the bikes and have covered parking, too. We would definitely stay here again!"
United States
Melanie K.
The price is AU$1,209
includes taxes & fees
2 Dec - 3 Dec
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A clear swimming pool with lounge chairs and palm trees.

16. 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 AU$848
includes taxes & fees
17 Nov - 18 Nov
Slice of Paradise
A modern kitchen with a large island, bar stools, and a built-in TV.

17. Catchlight House at Lunara Bay

Catchlight House at Lunara Bay
Raccoon Key
9.4 out of 10, Exceptional, (12 reviews)
"Perfect for our group of 15. Everything about the experience was top notch!"
United States
Brenda W.
Catchlight House at Lunara Bay
Property Overview

18. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
The price is AU$1,977
includes taxes & fees
4 Nov - 5 Nov
Aquaria House at Lunara Bay
Property Overview

19. Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (35 reviews)
"Property was good would stay here again!"
United States
Richard K.
The price is AU$2,028
includes taxes & fees
2 Nov - 3 Nov
Spindrift House at Lunara Bay
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

20. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is AU$2,215
includes taxes & fees
5 Nov - 6 Nov
Evershore House Pool Parking Dock
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fleming Key Hotel Reviews

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"I love that it's right on the water and I'm able to use the amenities at the neighboring resort"
Kelli 2-night trip
Posted 1 hour ago
The Reach Key West, Curio Collection by Hilton

Find out more about Fleming Key

Fleming Key Holiday Homes information

Number of reviews
533
Accommodation
795 Holiday Homes
Lowest Price
AU$416
Highest Price
AU$2,253

Explore a world of travel with Expedia