Default HTG hotel image

Fleming Key Vacation Rentals

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

Our top choices for Fleming Key vacation 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 P6,139
P17,604 total
includes taxes & fees
Oct 6 - Oct 7
Aqua Lodges at Hurricane Hole Marina
Exterior

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 P12,173
P19,506 total
includes taxes & fees
Oct 7 - Oct 8
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 P44,245
P74,809 total
includes taxes & fees
Oct 14 - Oct 15
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
Coconut Mallory Marina and Resort Condo
Room

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 P11,560
P18,817 total
includes taxes & fees
Oct 1 - Oct 2
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 P15,232
P25,439 total
includes taxes & fees
Oct 5 - Oct 6
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 P15,505
P31,142 total
includes taxes & fees
Oct 13 - Oct 14
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 P17,476
P35,021 total
includes taxes & fees
Oct 5 - Oct 6
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 P20,197
P35,175 total
includes taxes & fees
Oct 1 - Oct 2
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 P20,060
P37,928 total
includes taxes & fees
Oct 13 - Oct 14
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 P26,793
P53,805 total
includes taxes & fees
Oct 5 - Oct 6
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 P12,240
P26,224 total
includes taxes & fees
Oct 1 - Oct 2
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 P15,436
P36,047 total
includes taxes & fees
Oct 5 - Oct 6
The Grenada Suite Pool View Private Balcony
Exterior

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 P11,431
P18,676 total
includes taxes & fees
Oct 1 - Oct 2
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 P15,790
P23,182 total
includes taxes & fees
Oct 7 - Oct 8
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 P14,076
P21,254 total
includes taxes & fees
Oct 7 - Oct 8
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
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 P32,573
P57,401 total
includes taxes & fees
Oct 5 - Oct 6
Sunnyside Up by Brightwild Pool Parking
Exterior

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 P16,402
P31,610 total
includes taxes & fees
Oct 7 - Oct 8
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 P39,373
P69,203 total
includes taxes & fees
Oct 4 - Oct 5
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.
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

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."
Krystal 1-night trip
Posted less than an hour ago
Parrot Key Hotel & Villas

Find out more about Fleming Key

Search for holiday rentals in Fleming Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Fleming Key using one of the methods below:

  • View our selection of featured holiday rentals in Fleming Key
  • Use the map to find apartments and other holiday homes in the Fleming Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Fleming Key while they last

Look no further and take a look at our great range of rental properties in Fleming Key!