Discover a selection of 5,000 vacation rentals in Monroe County that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $166 per night, and houses and condos are popular options for a stay in Monroe County. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Monroe County
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How many vacation rentals are available around Monroe County?

Our 2021 property listings offer a large selection of 4,754 vacation rentals around Monroe County. From 2,936 house rentals to 1,306 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Explore destinations around Monroe County

Key West
1,859 vacation rentals
Key Largo
1,152 vacation rentals
Islamorada
1,148 vacation rentals
Marathon
1,254 vacation rentals
Key Colony Beach
1,227 vacation rentals
Tavernier
1,108 vacation rentals
Cudjoe Key
399 vacation rentals
Little Torch Key
336 vacation rentals
Key West Naval Station
1,865 vacation rentals
Big Pine Key
641 vacation rentals
Summerland Key
381 vacation rentals
Sugarloaf Key
853 vacation rentals
Duval Street
1,606 vacation rentals
Big Torch Key
380 vacation rentals
Middle Torch Key
376 vacation rentals
Ramrod Key
260 vacation rentals
Marathon Shores
1,009 vacation rentals
Lower Sugarloaf Key
284 vacation rentals
Upper Sugarloaf Key
336 vacation rentals