13946+ Private Villas and Holiday Rentals in Monroe County |
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  3. Monroe County

Monroe County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Monroe County

Discover more than 13946 vacation rentals available in Monroe County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Monroe County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Monroe County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Monroe County. On average, places to stay near Monroe County offer 830.85 ft², with nightly prices averaging US $661.

With Casai, finding and comparing holiday rentals in Monroe County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Monroe County

Type Count
Vacation Homes 8473
Holiday Apartments 1317
Villas 358
Cottages 280

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Monroe County.

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

Top Attractions Around Monroe County, FL

Casai offers a large selection of top attractions around Monroe County . Research things to do on your vacation before you visit Monroe County.


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

Other Places to Stay in Monroe County, FL


Florida Keys 8,923 Properties
Lower Florida Keys 3,872 Properties
Key West 3,057 Properties
Key West Historic District 2,386 Properties
Old Town 2,334 Properties
Duval Street 1,733 Properties
Marathon 1,606 Properties
Pretty Joe Rock 1,480 Properties
Key Largo 1,296 Properties
Downtown 1,006 Properties
Islamorada 888 Properties
Lower Keys 862 Properties

Frequently Asked Questions About Monroe County?

What are the top holiday rentals in Monroe County?

With numerous options available in Monroe County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Monroe County:

How many holiday rentals have private pools in Monroe County?

Discover a selection of holiday rentals with private pools near Monroe County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Monroe County are best for families?

If you're searching for a family-friendly holiday home in Monroe County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Monroe County:

How many Casai.com holiday rentals are available in Monroe County?

As of 2026, Casai boasts over 13946 properties listed in the Monroe County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Monroe County.


People Also Ask

There are 13946 Monroe County, FL Holiday Rentals

Recently Booked Holiday Rentals in Monroe County