Skip to content

Vacation rentals in Monroe County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monroe County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Hotel room in Key West
The Sanchez House Room #3
There is no better welcome to Key West than staying in local and famous folk artist Mario Sanchez's birth home. This home was built in the 1860's in the heart of the historic Gato and Merrero cigar factory villages. Featuring original Dade County pine construction, and located right on historic Duval Street, the Sanchez House is guaranteed to offer the historic atmosphere and living a part of Key West many visitors want to experience. Sit on the balcony and enjoy the trade winds & Ocean Breeze.
$161 per night
SUPERHOST
Townhouse in Key West
Poolside Cottage #412
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!
$198 per night
SUPERHOST
Private room in Key West
Mallory House Room #1
There is no better place for your Key West stay than Mallory House. This historic circa 1890’s home is located on Duval Street in the Gato Cigar Factory Village. Mallory House is steps away from famous attractions, restaurants, cafés, bars and shops. Stay within close proximity to the Southernmost point and beach, the Hemingway house and lighthouse. Enjoy a complimentary cup of coffee on our spacious balcony overlooking world famous Duval Street.
$166 per night
SUPERHOST

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Monroe County

Rental unit in Key West
Duval Balcony - Street Suite
$218 per night
SUPERHOST
Serviced apartment in Marathon
Knight's Key Suites Deluxe King w/Kitchen
$113 per night
Hotel room in Key West
Cabana Inn King Room (A) with Free Breakfast
$145 per night
Condo in Key West
Key West Studio a short walk from Higgs & Duval
$138 per night
Serviced apartment in Marathon
Knight's Key Suites Deluxe Double w/Kitchen
$124 per night
Cottage in Marathon
Cottage 08
$140 per night
Rental unit in Key West
At Mine | Key West Suite steps from Duval Street
$139 per night
SUPERHOST
Hotel room in Key West
Mallory House Room #3
$166 per night
SUPERHOST
Hotel room in Key West
The Sanchez House Room #1
$151 per night
SUPERHOST
Townhouse in Key West
Poolside Cottage #411
$220 per night
SUPERHOST
Hotel room in Key West
Cabana Inn King Room #411 with Free Breakfast
$145 per night
Houseboat in Big Pine Key
One Bedroom Aqualodge - # 7 Cobia Big Pine Key, FL
$130 per night
  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County