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
  • 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 homes

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.4 out of 10, Good, (38 reviews)
"Our stay was good. Yacht was as described. There were fans provided in the bedrooms downstairs so we were comfortable. There is an info book provided which helped a lot. "
United States
Faith C.
The price is AU$599
includes taxes & fees
13 July - 14 July
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is AU$1,156
includes taxes & fees
1 July - 2 July
Starlight Serenity - Hideaway w Stunning Views

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$956
includes taxes & fees
1 July - 2 July
Starlight Serenity - Hideaway with Stunning Views

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is AU$849
includes taxes & fees
16 June - 17 June
Paradise found

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (65 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is AU$432
includes taxes & fees
21 June - 22 June
Poolside Cottage #411

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, (251 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is AU$478
includes taxes & fees
2 July - 3 July
Feb 3-10 $245 off the rates close beach full kitchen & patio

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
9.8 out of 10, Exceptional, (16 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is AU$707
includes taxes & fees
13 July - 14 July
Road's End | Prime Old Town Location! Updated Home w/ Pool

Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (31 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is AU$432
includes taxes & fees
16 June - 17 June
Poolside Cottage #412

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is AU$2,553
includes taxes & fees
17 June - 18 June
Springtide House at Lunara Bay

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$2,863
includes taxes & fees
29 June - 30 June
Capmar House at Lunara Bay

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (23 reviews)
"Great place nice and clean easy access to the pool short drive to the beach"
United States
Nathan W.
The price is AU$1,381
includes taxes & fees
16 June - 17 June
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (24 reviews)
"Host was very welcoming and flexible. "
United States
Chad C.
The price is AU$2,770
includes taxes & fees
21 June - 22 June
The Seagate Estate at Lunara Bay

Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Great host!"
United States
Mario C.
The price is AU$2,852
includes taxes & fees
14 July - 15 July
Spindrift House at Lunara Bay

Crestwood House at Lunara Bay

Crestwood House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (2 reviews)
"The house and property was perfect for 4 adults and 4 kids. Gourmet kitchen for great breakfasts to start the day. Grill for cookouts and swimming in the early evenings. Good proximity to downtown key west, but far enough away for quiet time. Would stay again."
United States
Vicki L.
The price is AU$3,302
includes taxes & fees
17 June - 18 June
Crestwood House at Lunara Bay

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful home with great outdoor space and we loved the pool and private dock"
United States
Sharon L.
The price is AU$4,432
includes taxes & fees
21 June - 22 June
The Shellstone House at Solaire Lunara Bay

Floralee House at Lunara Bay

Floralee House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful host, smooth check in, very timely communications, great amenities, highly recommend it"
Canada
Marc D.
The price is AU$3,806
includes taxes & fees
13 July - 14 July
Floralee House at Lunara Bay

The Sunray Home at Lunara Bay

The Sunray Home at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful and well maintained "
United States
Dr. T.
The price is AU$4,648
includes taxes & fees
13 July - 14 July
The Sunray Home at Lunara Bay

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is AU$2,287
includes taxes & fees
16 June - 17 June
Private and Exclusive Beach Getaway

Palmgale Estate at Lunara Bay

Palmgale Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (11 reviews)
"Loved the fact that each bedroom had a private bathroom. This house is great for large family. "
United States
Sari v.
The price is AU$3,698
includes taxes & fees
28 June - 29 June
Palmgale Estate at Lunara Bay

Larkshine House at Lunara Bay

Larkshine House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (10 reviews)
"The house was super clean!! Great place to stay!!"
United States
Kami C.
The price is AU$4,533
includes taxes & fees
21 June - 22 June
Larkshine House at Lunara Bay
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

Fleming Key Holiday Homes information

Number of reviews
Accommodation
Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia