Fleming Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Fleming Key holiday rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (176 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is HK$1,640
HK$3,156 total
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (29 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is HK$2,235
HK$4,301 total
includes taxes & fees
2 Mar - 3 Mar
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (43 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is HK$3,282
HK$4,161 total
includes taxes & fees
25 Feb - 26 Feb
Living the Dream Key West Style

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is HK$4,254
HK$8,865 total
includes taxes & fees
20 Feb - 21 Feb
Private and Exclusive Florida Keys Getaway

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is HK$3,989
HK$7,098 total
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway w Stunning Views

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Place is perfect"
United States
Ryan S.
The price is HK$1,641
HK$3,503 total
includes taxes & fees
2 Mar - 3 Mar
Balcony, Pool, & Near Duval - Curry House Room 8

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is HK$6,833
HK$12,617 total
includes taxes & fees
18 Feb - 19 Feb
The Lighthouse - Beach Houses Key West

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (44 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is HK$10,481
HK$18,557 total
includes taxes & fees
12 Mar - 13 Mar
Springtide House at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is HK$6,245
HK$12,924 total
includes taxes & fees
12 Feb - 13 Feb
The Seagate Estate at Lunara Bay

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (143 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is HK$1,711
HK$3,871 total
includes taxes & fees
4 Mar - 5 Mar
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is HK$5,462
HK$12,369 total
includes taxes & fees
17 Feb - 18 Feb
Capmar House at Lunara Bay

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West
Stock Island
The price is HK$2,138
HK$3,755 total
includes taxes & fees
11 Feb - 12 Feb
3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West

Great Family Vacation Rental.

Great Family Vacation Rental.
Stock Island
8.8 out of 10, Excellent, (15 reviews)
"Enjoyed staying here super clean and well stocked!"
Canada
Kirsty E.
The price is HK$2,735
HK$4,890 total
includes taxes & fees
3 Mar - 4 Mar
Great Family Vacation Rental.

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is HK$7,024
HK$15,525 total
includes taxes & fees
17 Feb - 18 Feb
Suncoast House at Lunara Bay

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 HK$4,573
HK$7,043 total
includes taxes & fees
11 Feb - 12 Feb
Grand Marina Suite by Brightwild Waterfront

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Stock Island
9.6 out of 10, Exceptional, (120 reviews)
"Great location, close to everything family had a great time."
United States
rafael m.
The price is HK$3,203
HK$6,042 total
includes taxes & fees
27 Feb - 28 Feb
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Comfortable Condo with Pool, Private Balcony, & Beach Access

Comfortable Condo with Pool, Private Balcony, & Beach Access
Beachside
8.6 out of 10, Excellent, (140 reviews)
"Beautiful property! Pool was phenomenal. There is a men’s and a Womens sauna separately. The common area greenery is beautiful. Thank you"
United States
Amanda G.
The price is HK$3,619
HK$8,037 total
includes taxes & fees
11 Mar - 12 Mar
Comfortable Condo with Pool, Private Balcony, & Beach Access

Feb 3-10 $245 off the rates close beach full kitchen & patio

Feb 3-10 $245 off the rates close beach full kitchen & patio
Old Town Key West
9.6 out of 10, Exceptional, (242 reviews)
"Great locationPlace looked like picsGreat host"
United States
derek a.
The price is HK$2,258
HK$4,100 total
includes taxes & fees
11 Mar - 12 Mar
Feb 3-10 $245 off the rates close beach full kitchen & patio

Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
The price is HK$2,742
HK$5,261 total
includes taxes & fees
27 Feb - 28 Feb
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (27 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is HK$5,462
HK$12,369 total
includes taxes & fees
18 Feb - 19 Feb
Evershore Estate at Lunara Bay | Wellness Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Fleming Key Hotel Reviews

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!