Default HTG hotel image

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, (190 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is HK$596
HK$1,985 total
includes taxes & fees
30 Jun - 1 Jul
Aqua Lodges at Hurricane Hole Marina

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)
"It was a great experience staying on against All Odds II.We had a challenge with the tv, but other than that great. We were able to use the hotel pool and shuttle which was a plus."
United States
Barbara C.
The price is HK$1,427
HK$3,290 total
includes taxes & fees
30 Jun - 1 Jul
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (132 reviews)
"Great place to stay"
United States
walter l.
The price is HK$861
HK$2,277 total
includes taxes & fees
8 Jul - 9 Jul
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (60 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is HK$2,509
HK$3,184 total
includes taxes & fees
29 Jun - 30 Jun
Living the Dream Key West Style

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (105 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
The price is HK$807
HK$2,208 total
includes taxes & fees
29 Jun - 30 Jun
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

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$2,967
HK$5,244 total
includes taxes & fees
6 Jul - 7 Jul
Grand Marina Suite by Brightwild Waterfront

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 HK$2,345
HK$4,813 total
includes taxes & fees
1 Jul - 2 Jul
Paradise found

The Grand Turk | Spectacular Sunset View, Private

The Grand Turk | Spectacular Sunset View, Private
Key West
9.0 out of 10, Wonderful, (17 reviews)
"Great location!"
United States
Sheila
The Grand Turk | Spectacular Sunset View, Private

Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (27 reviews)
"Location was perfect. The condo was very clean and all the little touches were much appreciated! Very pleasant stay. Communication with our host was excellent with quick responses. Next visit to Key West we definitely will be looking to stay here again. "
United States
Anonymous traveller
The price is HK$1,353
HK$3,484 total
includes taxes & fees
1 Jul - 2 Jul
Waterfront Condo Dock Pool Near Duval St

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (31 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is HK$1,450
HK$4,057 total
includes taxes & fees
22 Jul - 23 Jul
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"A good value for the travel dollar."
United States
sandra j.
The Cat Island Suite | Charmingly Renovated w/ Pool

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (50 reviews)
"Good location and value"
United States
Dan W.
The price is HK$932
HK$2,842 total
includes taxes & fees
1 Jul - 2 Jul
VanGogh Studio | Updated, Old Town, Heated Pool

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (32 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
The price is HK$2,188
HK$4,736 total
includes taxes & fees
7 Jul - 8 Jul
Grand Marina Suite - Poolside & Waterfront Condo

Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
9.0 out of 10, Wonderful, (33 reviews)
"Very nice place to stay, great pool area and great room. "
United States
Blake
The price is HK$850
HK$2,725 total
includes taxes & fees
29 Jun - 30 Jun
Leo's Lodge | Newly Updated!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Great location"
United States
Glen V.
The price is HK$932
HK$3,286 total
includes taxes & fees
2 Jul - 3 Jul
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

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$2,084
HK$3,048 total
includes taxes & fees
29 Jun - 30 Jun
Resort View 1BR Suite

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, (252 reviews)
"Loved our stay here!"
United States
Kristin E.
The price is HK$1,023
HK$2,544 total
includes taxes & fees
2 Jul - 3 Jul
Feb 3-10 $245 off the rates close beach full kitchen & patio

Prime Downtown Key West Spot - The Cozy Little Cottage!

Prime Downtown Key West Spot - The Cozy Little Cottage!
Old Town Key West
9.6 out of 10, Exceptional, (49 reviews)
"Great location, cute space"
United States
Owen
The price is HK$1,294
HK$2,627 total
includes taxes & fees
20 Jul - 21 Jul
Prime Downtown Key West Spot - The Cozy Little Cottage!

Poolside Cottage #412

Poolside Cottage #412
Key West
9.2 out of 10, Wonderful, (32 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is HK$1,306
HK$2,405 total
includes taxes & fees
1 Jul - 2 Jul
Poolside Cottage #412

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (440 reviews)
"Great location within walking distance to both ends of Duval. The bikes were nice as well and the unit was very clean. Enjoyed our stay."
United States
Jeff T.
The price is HK$1,122
HK$2,323 total
includes taxes & fees
20 Jul - 21 Jul
Steps from Duval, Pool on Site & Bikes Included!
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!

Explore a world of travel with Expedia