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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 rentals

A pool area with a wooden deck, lounge chairs, and a waterfall feature.

1. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
United States
Melissa
The price is Rp9.394.966
Rp13.652.627 total
includes taxes & fees
13 Nov - 14 Nov
Lighthouse Suites Collection
A row of floating houses with balconies, connected by walkways, on calm water.

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is Rp1.942.473
Rp5.291.055 total
includes taxes & fees
31 Oct - 1 Nov
Aqua Lodges at Hurricane Hole Marina
A waterfront property with a large building featuring balconies and a covered area, boats docked in front, and palm trees in the background.

3. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is Rp5.885.935
Rp11.028.968 total
includes taxes & fees
31 Oct - 1 Nov
Grand Marina Suite by Brightwild Waterfront
A modern house with a swimming pool, a balcony, and a well-maintained garden.

4. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is Rp12.822.859
Rp21.680.516 total
includes taxes & fees
2 Nov - 3 Nov
Contra House Key West
A dining area with a wooden table and chairs, a blue sofa, and a view of the outdoors through a glass door.

5. Sunnyside Up by Brightwild Pool Parking

Sunnyside Up by Brightwild Pool Parking
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
The price is Rp12.440.440
Rp19.708.650 total
includes taxes & fees
22 Nov - 23 Nov
Sunnyside Up by Brightwild Pool Parking
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

6. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is Rp4.398.730
Rp10.090.411 total
includes taxes & fees
30 Nov - 1 Dec
The Grenada Suite Pool View Private Balcony
A balcony with a wicker sofa and a palm tree, overlooking a street with buildings and a CVS store.

7. Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
The price is Rp8.991.257
Rp16.628.161 total
includes taxes & fees
2 Nov - 3 Nov
Duval Dream Loft by Brightwild Right on Duval
A white two-story house with a balcony and a swimming pool.

8. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is Rp13.932.505
Rp28.243.010 total
includes taxes & fees
4 Nov - 5 Nov
Capmar House by Brightwild Huge Home Pool
A white house with a porch, surrounded by tropical plants and a stone pathway.

9. New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2 reviews)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is Rp6.937.240
Rp10.089.657 total
includes taxes & fees
30 Nov - 1 Dec
New The Cottage at James House
A modern kitchen with a large island, built-in appliances, and pendant lighting.

10. Cloud Suite on Duval Luxury Condo Epic Location

Cloud Suite on Duval Luxury Condo Epic Location
2.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Great space, amazing location, could be a bit cleaner. "
Canada
Marcus
The price is Rp12.886.060
Rp20.781.288 total
includes taxes & fees
17 Nov - 18 Nov
Cloud Suite on Duval Luxury Condo Epic Location
A cozy living area with a sofa, a dining table with chairs, and a television mounted on the wall.

11. Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
The price is Rp13.932.505
Rp25.957.747 total
includes taxes & fees
17 Nov - 18 Nov
Commodore s Cove by Brightwild Epic Location
A porch with a white railing, a pink door, and a white fence.

12. New Rose Petal Petite Suite - Pool Parking

New Rose Petal Petite Suite - Pool Parking
2.0 star property
Key West Historic District
The price is Rp4.573.091
Rp8.229.831 total
includes taxes & fees
29 Nov - 30 Nov
New Rose Petal Petite Suite - Pool Parking
A wooden pedestrian bridge over a water body, surrounded by lush greenery and palm trees.

13. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is Rp5.504.942
Rp11.334.899 total
includes taxes & fees
18 Nov - 19 Nov
Tortuga Suite Sparkling Pool Hot Tub
A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

14. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is Rp7.092.164
Rp12.206.418 total
includes taxes & fees
9 Nov - 10 Nov
The Bartlum Luxury Studio In Prime Location
A covered porch with two black chairs and a table, white building with a door and windows, and palm trees in the background.

15. The Mesa House by Brightwild Close to Duval

The Mesa House by Brightwild Close to Duval
2.0 star property
Key West Historic District
The price is Rp15.133.874
Rp28.337.655 total
includes taxes & fees
9 Nov - 10 Nov
The Mesa House by Brightwild Close to Duval
A spacious living area with a sofa, glass coffee table, and a kitchen with sliding doors leading to a balcony.

16. Contra House by Brightwild Luxury Home w Pool

Contra House by Brightwild Luxury Home w Pool
2.0 star property
Old Town Key West
6.0 out of 10, (1 review)
"The pool was very dirty with lots of leaves & the pool spa did not work upon arrival. Contacted mgt company several times about the spa. They sent someone out but he was not able to fix it. The worst issues were the showers as the settings were too hot & the temperature could not be adjusted. "
United States
Marlene
Contra House by Brightwild Luxury Home w Pool
A two-story building with a white picket fence, surrounded by lush greenery and palm trees.

17. Sky Loft by Brightwild Penthouse in Prime Spot

Sky Loft by Brightwild Penthouse in Prime Spot
2.0 star property
Old Town Key West
Sky Loft by Brightwild Penthouse in Prime Spot
A covered porch with a table and chairs, overlooking a street with houses and cars.

18. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is Rp5.561.369
Rp10.027.223 total
includes taxes & fees
9 Nov - 10 Nov
Banana Split by Brightwild Pool Grill
A bedroom with a bed, a ceiling fan, a painting, and a window.

19. Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is Rp8.521.811
Rp15.642.983 total
includes taxes & fees
10 Nov - 11 Nov
Sea Breeze by Brightwild Off-street Parking
A white house with a porch, palm trees, and a white picket fence.

20. Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is Rp6.975.970
Rp12.075.700 total
includes taxes & fees
2 Nov - 3 Nov
Mesa House Uno by Brightwild Perfect 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 Fleming Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"This was our second year staying here for Fantasy Fest. We love the staff! Sonja was an absolute gem the entire time. She welcomed us with the best smile every day and offered to take our picture as we passed by to our events. The grounds are impeccably kept and a great location, we prefer to by a little away from Duval. Breakfast hit the mark except we did miss the turmeric and ginger shots this year."
Marnie 4-night trip
Posted less than an hour ago
Winslow's Bungalows - Key West Historic Inns

Find out more about Fleming Key

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