Owner Direct Vacation
Rentals in Monroe County
The Best Owner Direct Vacation Rentals in Monroe County. Explore thousands of vacation home rentals, large cabins, and villas near Monroe County
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Explore the Best Monroe County Vacation Homes
Looking for the perfect place to stay in Monroe County? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Monroe County character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Monroe County Vacation Rentals
What makes our vacation homes stand out?

Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.

Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Monroe County
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Popular Neighborhoods for Monroe County Vacation Rentals
What are the best areas to stay in Monroe County
Discover the top neighborhoods in Monroe County and choose a place that suits your stay.
Florida Keys
Florida Keys VACATION RENTALSLower Florida Keys
Lower Florida Keys VACATION RENTALSKey West
Key West VACATION RENTALSKey West Historic District
Key West Historic District VACATION RENTALSOld Town
Old Town VACATION RENTALSDuval Street
Duval Street VACATION RENTALSMarathon
Marathon VACATION RENTALSPretty Joe Rock
Pretty Joe Rock VACATION RENTALSKey Largo
Key Largo VACATION RENTALSDowntown
Downtown VACATION RENTALSIslamorada
Islamorada VACATION RENTALSLower Keys
Lower Keys VACATION RENTALSThursday Jan 29
Monroe County, Florida







Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Monroe County vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Monroe County
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How to Reserve Your Monroe County Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Monroe County Vacation Rental FAQs
1. What are the top vacation rentals in Monroe County?
There are a lot of options in Monroe County. If you plan on staying in the Monroe County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Monroe County:
- Almond Tree Inn Hotel - Adults Only
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Summer Fun Awaits! Clean and Cozy w TOP FLOOR VIEWS.Your Home Away From Home!
- Oceanfront Key Largo Paradise~Private Beach~Pool~Tennis~Marina~Restaurant
- Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
- Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
- Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
- 🌴 Coco Plum Paradise 🌴 Private Bayfront Home Pool Hot Tub Dock View
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
2. How many vacation rentals have private pools in Monroe County?
There are 2966 vacation rentals with private pools near Monroe County. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Monroe County are best for families?
If you are looking for a family-friendly vacation home in Monroe County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Monroe County:
4. How many vacation rentals are available in Monroe County?
Currently, the total number of properties listed in 2026 is over 14086 in the Monroe County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Monroe County.