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Fleming Key Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Fleming Key holiday rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is HK$699
HK$2,125 total
includes taxes & fees
29 Sept - 30 Sept
Aqua Lodges at Hurricane Hole Marina

2. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is HK$1,424
HK$2,331 total
includes taxes & fees
29 Sept - 30 Sept
Island View 1BR Residence With Balcony
A modern house with a swimming pool, a balcony, and a well-maintained garden.

3. 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 HK$5,546
HK$9,377 total
includes taxes & fees
11 Oct - 12 Oct
Contra House Key West
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

4. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is HK$7,759
HK$10,297 total
includes taxes & fees
29 Sept - 30 Sept
Coconut Mallory Marina and Resort Condo

5. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is HK$1,424
HK$2,331 total
includes taxes & fees
29 Sept - 30 Sept
Resort View 1BR Suite
A white house with a porch, surrounded by tropical plants and a stone pathway.

6. 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 HK$2,013
HK$3,306 total
includes taxes & fees
1 Oct - 2 Oct
New The Cottage at James House
A covered porch with a table and chairs, overlooking a street with houses and cars.

7. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is HK$1,535
HK$3,445 total
includes taxes & fees
29 Sept - 30 Sept
Banana Split by Brightwild Pool Grill
A white house with a porch, palm trees, and a white picket fence.

8. 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 HK$1,996
HK$4,172 total
includes taxes & fees
29 Sept - 30 Sept
Mesa House Uno by Brightwild Perfect Location
A two-story building with a blue facade, a white picket fence, and palm trees.

9. Sky Loft by Brightwild Penthouse in Prime Spot

Sky Loft by Brightwild Penthouse in Prime Spot
2.0 star property
Old Town Key West
The price is HK$2,192
HK$4,028 total
includes taxes & fees
29 Sept - 30 Sept
Sky Loft by Brightwild Penthouse in Prime Spot
A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

10. 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 HK$2,379
HK$4,603 total
includes taxes & fees
14 Oct - 15 Oct
The Bartlum Luxury Studio In Prime Location
A balcony with a wicker sofa and a palm tree, overlooking a street with buildings and a CVS store.

11. 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 HK$3,036
HK$6,383 total
includes taxes & fees
29 Sept - 30 Sept
Duval Dream Loft by Brightwild Right on Duval
A view through white blinds of a swimming pool area with a hot tub, surrounded by palm trees and a white fence.

12. Poolside Retreat by Brightwild Cottage w Pool

Poolside Retreat by Brightwild Cottage w Pool
3.0 star property
Old Town Key West
2.0 out of 10, (2 reviews)
"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...
United States
Julia
The price is HK$1,535
HK$3,289 total
includes taxes & fees
1 Oct - 2 Oct
Poolside Retreat by Brightwild Cottage w Pool
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

13. 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 HK$1,936
HK$4,521 total
includes taxes & fees
30 Sept - 1 Oct
The Grenada Suite Pool View Private Balcony

14. Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is HK$1,424
HK$2,331 total
includes taxes & fees
29 Sept - 30 Sept
Resort View 1BR Suite With Direct Pool Access
A beach view with palm trees, a wooden pier, and a sunset over the water.

15. Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is HK$2,019
HK$2,951 total
includes taxes & fees
29 Sept - 30 Sept
Ocean Front 1BR Suite With Direct Beach Access
A room with a bed, two armchairs, a small table, and a window with a view of palm trees and the sea.

16. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is HK$1,742
HK$2,640 total
includes taxes & fees
29 Sept - 30 Sept
Ocean Front One Bedroom Residence
A wooden pathway leading to a beach with palm trees and a clear blue sky.

17. Island Time Gorgeous Condo Steps To The Beach

Island Time Gorgeous Condo Steps To The Beach
2.0 star property
Key West
The price is HK$1,927
HK$4,928 total
includes taxes & fees
29 Sept - 30 Sept
Island Time Gorgeous Condo Steps To The Beach
A dining area with a wooden table and chairs, a blue sofa, and a view of the outdoors through a glass door.

18. 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 HK$4,060
HK$7,170 total
includes taxes & fees
5 Oct - 6 Oct
Sunnyside Up by Brightwild Pool Parking

19. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is HK$2,111
HK$4,025 total
includes taxes & fees
29 Sept - 30 Sept
Two Bedroom Residence With Balcony
A spacious living room with a wooden ceiling, large windows, a blue sofa, and a wooden coffee table.

20. Kamp by Brightwild Rooftop Penthouse On Duval

Kamp by Brightwild Rooftop Penthouse On Duval
2.0 star property
Old Town Key West
The price is HK$3,070
HK$6,578 total
includes taxes & fees
29 Sept - 30 Sept
Kamp by Brightwild Rooftop Penthouse On Duval
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"This was the first time we've stayed at a Margaritaville but definitely won't be the last. The staff were all very friendly and helpful. The room was clean and a great size. Having a shuttle to downtown was wonderful. Saved a ton of time and money not having to look for and pay for parking. The bus driver Johnny was great. Lots of recommendations for places to eat. The pool area was nice and the beach was right across the road. Absolutely nothing wrong the entire time we stayed there."
Kimberly 4-night trip
Posted less than an hour ago
Margaritaville Beach House Key West

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