Spend Your Winter in These Key West Monthly Rentals

You are here

20 Dec 2019
Related Items: 
Key West Vacation Rentals

Ditch the cold and come spend your winter in Key West, Florida. Our Key West monthly rentals are located throughout the island, whether you want to be in the center of Old Town or in a quiet neighborhood away from the action. This time of the year there are plenty of things to do in Key West, like the Key West Food & Wine Festival, Annual Old Days Festival in Key West, and the Conch Shell Blowing Contest.

Coral Villa

Coral Villa Key West

Coral Villa is a 3 bedroom, 3 bathroom vacation rental with space for 6 guests. Located in the Coral Hammock community, this home is near shopping, dining, and attractions while still feeling like you’re secluded enough to enjoy peace and quiet. You’ll be surrounded by lush tropical landscaping so you can sip on your morning coffee or an evening cocktail while listening to the wind in palms. This gated community has a spacious pool with shaded cabana areas and lounge chairs for sunbathing. 

Book Coral Villa

Poolside Paradise

Poolside Paradise Key West

Poolside Paradise is a 2 bedroom, 2 bathroom home with space for 4 guests, and it’s pet-friendly. Located in the center of the island, this home sits on a quiet residential block but is close enough to the water and Key West Historic District to get to all the best things to do. Sit back and relax at your private pool and patio area and you’ll wish you never had to leave. 

Book Poolside Paradise

Sunny View

Sunny View Key West

Sunny View is a 1 bedroom, two bathroom home with enough space for two guests. Enjoy this tropical oasis just a short walk from the center of Duval Street in Old Town, Key West. This cottage rental has a fenced yard with a barbecue and sitting area to relax and unwind when you’re done exploring the area. 

Book Sunny View

Under the Palms

Under the Palms Key West

Under the Palms is a 2 bedroom, 2 bathroom vacation rental for 4 guests. This pet-friendly home is on a quiet street in midtown Key West. Featuring a backyard, grill area, and pool, this rental is great for entertaining friends and family. You’ll love this oasis that is just a short walk to the best bars and restaurants along Duval Street. 

Book Under the Palms

Paradise Palms

Paradise Palms Key West

Paradise Palms is a 2 bedroom, 2 bathroom rental home that sleeps 6 guests. Surrounded by lush, tropical foliage, this cottage features a cozy front porch and courtyard and an outdoor shower. Relax in this cute neighborhood home or go out on the town in Old Town. 

Book Paradise Palms

Plan Your Winter Vacation to Key West, Florida

There's still time to book the perfect Key West vacation rental for the winter season, whether you're staying for the whole season or just a quick getaway. 

Browse All Our Key West Monthly Rentals