13965+ Vacation Rentals & Holiday Homes in Monroe County |
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Monroe County Accommodations - Hotels & Rentals

About Monroe County Vacation Rentals

Discover More than 13965 Incredible Getaway Rentals Available in Monroe County. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Monroe County.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Monroe County, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Monroe County. The Average Size of Places to Stay Near Monroe County is 831.64 ft², with Prices Averaging US $660 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Monroe County. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Monroe County

Type Count
Vacation Homes 8488
Holiday Apartments 1317
Villas 358
Cottages 280

Use these Quick Filters to Find a Vacation Rental in Monroe County

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Monroe County with Online Reservations.

Weather in Monroe County, FL

View the weather forecast for Monroe County before booking your Monroe County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Monroe CountyGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Monroe CountyGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Duval Street
Smathers Beach
Southernmost Point
Mallory Square
Dry Tortugas National Park
South Beach
Sombrero Beach
John Pennekamp Coral Reef State Park
Higgs Beach
Bahia Honda State Park and Beach
Key West Harbour
Key West Aquarium
Ernest Hemingway Home and Museum
Jimmy Johnson's Big Chill
Dolphin Research Center
Fort Zachary Taylor Historic State Park
Theater of the Sea
Key West Butterfly and Nature Conservatory
Florida Keys Beaches
Seven Mile Bridge
Saddlebunch Keys
Key Largo Undersea Park
Harry S. Truman Little White House
Key West Shipwreck Museum
Flamingo Visitor Center
Dolphins Plus Bayside
Key West Golf Club
Key West Lighthouse and Keeper's Quarters Museum
Ripley's Believe It or Not

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Florida Keys 8,943 Properties
Lower Florida Keys 3,878 Properties
Key West 3,062 Properties
Key West Historic District 2,387 Properties
Old Town 2,335 Properties
Duval Street 1,731 Properties
Marathon 1,612 Properties
Pretty Joe Rock 1,485 Properties
Key Largo 1,300 Properties
Downtown 1,007 Properties
Islamorada 890 Properties
Lower Keys 864 Properties

Frequently Asked Questions About Monroe County?

What are the top hotels, lake houses & vacation rentals in Monroe County?

We provide an array of great vacation destinations in Monroe County. If you are looking to stay in or around the Monroe County area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Monroe County:

How many Hotels & Vacation Rentals have private pools in Monroe County?

We have 2957 Hotels & Vacation Rentals featuring a private pool in and near Monroe County. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Monroe County is best for families?

Searching for a family-friendly getaway in Monroe County? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Monroe County?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 13965 in the Monroe County area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Monroe County.


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