Book Villas in Monroe County, FL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top cities with Villas to explore in Monroe County

Key West
Villas
Top Villas in Monroe County

The Islands of Islamorada
82779 Old Hwy Islamorada FL
$658 nightly
The price is $740 total per night
$740 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Families will appreciate the playground and barbecue grills.
Pool
Hot Tub

TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking
Marathon FL
A marina and an outdoor pool are featured at this smoke-free villa. Families will appreciate the playground and onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and barbecue grills.
Pool
Hot Tub

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg
Duck Key FL
This villa features laundry facilities.
Washer
Dryer

Stunning Panoramic rooftop views from this gulf side Tuscan style Villa!
Marathon FL
A hot tub is featured at this villa, along with laundry facilities and barbecue grills.
Pool
Hot Tub

Seas the Keys Getaway
Duck Key FL
A gym is featured at this villa, along with laundry facilities.
Pool
Kitchen

Charming 3-bedroom villa with WiFi, AC in welcoming Marathon
Marathon FL
A hot tub is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Hot Tub

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Key West FL
This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key FL
$564 nightly
The price is $628 total per night
$628 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This villa features laundry facilities.
Kitchen
Washer

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Key West FL
$913 nightly
The price is $1,013 total per night
$1,013 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
A hot tub is featured at this villa, along with laundry facilities.
Pool
Hot Tub

DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included
Marathon FL
This villa features laundry facilities.
Pool
Kitchen
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.
Monroe County Villas essential information
Accommodation | 219 Villas |
|---|---|
Lowest Price | $628 |
Highest Price | $1,013 |
Popular accommodation | The Islands of Islamorada, TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking, Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg, Stunning Panoramic rooftop views from this gulf side Tuscan style Villa!, Seas the Keys Getaway, Charming 3-bedroom villa with WiFi, AC in welcoming Marathon, Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere, Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA, Two Bedroom Two Bath Poolside Villa Steps from Duval!, DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included, Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA, Two Bedroom Two Bath Balcony Villa Steps from Duval! |
More ways to wander Monroe County
Monroe County Flights
The best fares to get you there
Monroe County Hotels
Monroe County Vacation Rentals
Great Deals on Alternative Accommodations
Monroe County Car Rentals
Affordable cars to get you around town
Monroe County Vacations
Save more by combining flights, hotels and cars
Things to do in Monroe County
Explore More Ways to Travel with Travelocity
- Farmstay in Key West
- Apartments in Key West
- B&B in Key West
- Cabins in Key West
- Pod Hotels in Key West
- Condo Resorts in Key West
- Condos in Key West
- Cottages in Key West
- Cruise Ships in Key West
- Extended Stay Hotels in Key West
- Guest Houses in Key West
- Hostels in Key West
- All Inclusive Resorts & in Key West
- Beach Resorts & in Key West
- Key West Hotels
- Houseboats in Key West
- Inns in Key West
- Motels in Key West
- Vacation Homes in Key West
- Rv Parks in Key West
- Residences in Key West
- Resorts in Key West
- Treehouses in Key West
- Villas in Key West
- Vacation Homes in Dredgers Key
- Condos in Fleming Key
- Extended Stay Hotels in Fleming Key
- Hostels in Fleming Key
- Houseboats in Fleming Key
- Vacation Homes in Fleming Key
- Beach Resorts & in New Town
- Convention Center Hotels in New Town
- Gay Friendly Hotels in New Town
- Hotels with Pools in New Town
- Luxury Hotels in New Town
- Pet Friendly Hotels in New Town
- New Town Hotels
- Holiday Park Resorts in Flamingo
- Safari Camps in Flamingo
- Treehouses in Flamingo
- Hotels near Smathers Beach
- Cottages in Cow Key
- Houseboats in Cow Key
- Rv Parks in Cow Key
- Hotels near Duval Street
- Old Town Key West Hotels
- Beach Resorts & in Midtown
- Pet Friendly Hotels in Midtown
- Midtown Hotels
- Flights to Key West
- Flights from Key West Intl.
- American Airlines Miami (MIA) to Key West (EYW) flights
- Delta Atlanta (ATL) to Key West (EYW) flights
- Jetblue Airways Charleston (CHS) to Key West (EYW) flights
- Jetblue Airways New York (JFK) to Key West (EYW) flights
- Jetblue Airways Boston (BOS) to Key West (EYW) flights
- Jetblue Airways Sarasota (SRQ) to Key West (EYW) flights
- Silver Airways Tampa (TPA) to Key West (EYW) flights
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Austin (AUS) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Norfolk (ORF) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Louisville (SDF) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Knoxville (TYS) to Key West (EYW)
- Cheap Hotels in Key West
- Flights to Key West
- Car rentals at Key West Airport (EYW)
- Oceanfront Hotels in Key West
- All-inclusive Resorts in Key West
- Condos in Key West
- Hotels near Smathers Beach
- Visit Fort East Martello Museum and Gallery
- Hotels in Key West
- Beach Hotels in Key West
- Hotels in Key West Historic District
- Key West vacations
- Car rentals in Key West
- Hotels near Duval Street
- Houseboats in Key West








