Search Villas in Fleming Key
Change your mindBook hotels with free cancellation
Be pickySearch 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 villas
Villa in Old Town Key West
Two Bedroom Two Bath Balcony Villa Steps from Duval!10.0 out of 10, Exceptional, (43)
"The hosts were the best we have ever encountered. Their attention to detail surpassed all expectations. We will stay here again without hesitation. "
Barb B.
The price is NZ$1,732
includes taxes & fees
6 Jan - 7 Jan 2026
Villa in Old Town Key West
Poolside Queen Room Steps from Duval!10.0 out of 10, Exceptional, (1)
"Perfect location, awesome hosts, and the Key West Villas were wonderful. The pool area provided a tranquil area to relax."
Travis P.
The price is NZ$822
includes taxes & fees
8 Jan - 9 Jan 2026
Villa in Old Town Key West
Loft Villa Steps from Duval!10.0 out of 10, Exceptional, (17)
"Can’t say enough great things about this place. From the hosts to the property itself, top notch!"
Dave N.
The price is NZ$1,084
includes taxes & fees
5 Jan - 6 Jan 2026
Villa in Old Town Key West
Poolside King Room Steps from Duval!10.0 out of 10, Exceptional, (1)
"If you’re looking to stay in Old Town this is the perfect location. Pool right outside the room, FREE Happy Hour from 4-5 and very accommodating hosts. Good for families or couples alike. Awesome!"
Michael L R.
The price is NZ$867
includes taxes & fees
5 Jan - 6 Jan 2026
Villa in Old Town Key West
Poolside Studio Villa Steps from Duval!10.0 out of 10, Exceptional, (22)
"Great place to stay"
Benjamin K.
The price is NZ$862
includes taxes & fees
7 Jan - 8 Jan 2026
Villa in Old Town Key West
One Bedroom Deck Villa Steps from Duval!10.0 out of 10, Exceptional, (8)
"Beautiful property, clean and comfortable suite, friendly staff, fantastic hospitality, ideal central location! We'll be back!"
Tim P.
The price is NZ$1,082
includes taxes & fees
5 Jan - 6 Jan 2026
Villa in Old Town Key West
Two Bedroom Two Bath Poolside Villa Steps from Duval!10.0 out of 10, Exceptional, (48)
"Staff, accommodations and location were excellent. Would definitely stay there again."
Steve D.
The price is NZ$1,736
includes taxes & fees
21 Jan - 22 Jan 2026
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.
Find holiday rentals that suit your style
Aparthotels
Villas
Save an average of 15% on thousands of hotels when you're signed in
Top Fleming Key Hotel Reviews
Hyatt Centric Key West Resort and Spa
10/10 Excellent
Find out more about Fleming Key
Fleming Key Villas information
Number of reviews | 134 |
|---|---|
Accommodation | 17 Villas |
Lowest Price | NZ$822 |
Highest Price | NZ$1,736 |
Explore a world of travel with Expedia
- Apartments in Sugarloaf Key
- Cottages in Cudjoe Key
- Serviced Apartments in Key West
- Cottages in Key West
- Villas in Key West
- Apartments in Key West
- Guest Houses in Key West
- B&B in Key West
- Motels in Key West
- Resort in Key West
- Cabin Rentals in Key West
- Hostels in Key West
- Condo Rentals in Key West
- Houseboats in Key West
- Holiday Homes in Key West
- Resort in Little Torch Key
- Caravan Parks in Boca Chica Key
- Motels in Raccoon Key
- Cottages in Raccoon Key
- Resort in Lower Keys
- Motels in Lower Keys
- Cottages in Fleming Key
- Motels in Fleming Key
- Holiday Homes in Fleming Key
- Resort in Lower Florida Keys
- Caravan Parks in Lower Florida Keys
- Hostels in Lower Florida Keys
- Motels in Lower Florida Keys
- Resort in Key Haven
- Marriott Hotels & Resorts in Stock Island
- Hyatt Hotels in Key West
- Hilton Hotels in Key West
- Kimpton Hotels in Key West
- Sunset Key Hotels
- Truman Annex Hotels
- Hotels near Mel Fisher Maritime Museum
- New Town Hotels
- Hotels near Duval Street
- Midtown Hotels
- Old Town Key West Hotels
- Key West Hotels
- Hotels near Harry S. Truman Little White House
- Key West Historic District Hotels
- Hotels near Smathers Beach
- Beach Hotels in Key West
- Hotels with Pool in Key West
- Romantic Hotels in Key West
- Historic Hotels in Key West
- Family Hotels in Key West
- Ski Hotels in Key West
- Cheap Hotels in Key West
- Lgbt Welcoming Hotels in Key West
- Luxury Hotels in Key West
- Adventure Sport Hotels in Key West
- All Inclusive Hotels in Key West
- Pet Friendly Hotels in Key West
- Lgbt Welcoming Hotels in Key West Historic District
- Cheap Hotels in Key West Historic District
- Lgbt Welcoming Hotels in White Street Gallery District
- Flights to Key West
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from Lexington (LEX) to Key West (EYW)
- Flights from Salmon Arm (YSN) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Trinidad (TAD) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Henderson (HSH) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Tokyo (TYO) to Key West (EYW)
- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from Houston (HOU) to Key West (EYW)
- Flights from Orlando (ORL) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Gaithersburg (GAI) to Key West (EYW)
- Flights from Gainesville (GNV) to Key West (EYW)
- Flights from Naknek (NNK) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Montgomery (MGM) to Key West (EYW)
- Flights from Naples (NAP) to Key West (EYW)