Monroe County Vacation Rentals & Beach Homes

Find Island Stays Near Beaches, Boating & Florida Keys Adventures

90 stays availableCountywide

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About Monroe County

Guest reviews for Monroe County: 4.8 average from 397 reviews across 65 of 90 stays
Monroe County is Florida’s southernmost county and is best known as the home of the spectacular Florida Keys. The county encompasses the entire Florida Keys island chain, surrounding waters, and largely undeveloped mainland areas within Everglades National Park and Big Cypress National Preserve. The Florida Keys stretch for more than 100 miles and include famous destinations such as Key Largo, Islamorada, Marathon, Big Pine Key and the Lower Keys, and Key West. Visitors can enjoy snorkeling, diving, boating, fishing, kayaking, wildlife encounters, scenic drives, and laid-back island experiences surrounded by turquoise waters. Choosing a Monroe County vacation rental provides a convenient base for exploring the Florida Keys. From waterfront homes and beach stays to condos and island retreats, travelers can experience tropical scenery, outdoor adventures, local dining, and iconic destinations throughout one of Florida’s most distinctive vacation regions.

Overview

Discover Monroe County vacation rentals by owner in Florida, featuring beach homes, condos, waterfront stays, and family-friendly properties throughout the Florida Keys. Enjoy easy access to Key West, beautiful beaches, boating, fishing, snorkeling, and island attractions. With more space, privacy, and home-style amenities, Monroe County offers an ideal base for families, couples, and groups seeking a memorable Florida Keys vacation.

Things to do in Monroe County

Top experiences and activities around Monroe County.

  • Explore Key West

    Discover Key West for historic Old Town, Duval Street, Mallory Square sunsets, waterfront dining, museums, and colorful island architecture. It’s one of Monroe County’s signature vacation experiences.

  • Snorkel & Dive the Florida Keys

    Explore the Florida Keys’ coral reefs and clear waters through snorkeling and scuba diving. Key Largo, Islamorada, Marathon, and the Lower Keys offer excellent opportunities for marine-life encounters and underwater adventures.

  • Go Boating & Fishing

    Experience Monroe County from the water with boating, deep-sea fishing, backcountry fishing, kayaking, and paddleboarding. The Keys’ Atlantic Ocean and Florida Bay waters make water recreation a major part of any Florida Keys vacation.

Nearby attractions in Monroe County

Landmarks and day trips close to Monroe County.

Show nearby attractions
  • John Pennekamp Coral Reef State Park

    Located in Key Largo, this iconic park is famous for snorkeling, scuba diving, glass-bottom boat tours, coral reefs, and marine life, making it a must-visit Florida Keys attraction.

  • Bahia Honda State Park

    Discover beautiful beaches, turquoise waters, snorkeling, swimming, kayaking, and views of the historic Bahia Honda Bridge. It’s one of the standout natural attractions of the Lower Keys.

  • The Hemingway Home and Museum

    Explore Ernest Hemingway’s historic Key West residence and learn about the celebrated author’s years in the Florida Keys. It’s one of Key West’s best-known cultural landmarks.

  • Sunset Celebration at Mallory Square

    Experience one of Key West’s signature traditions with spectacular Gulf sunsets, street performers, local artists, and waterfront views at Mallory Square.

Popular neighbourhoods in Monroe County

Popular areas to base yourself in Monroe County.

Best time to visit Monroe County

When to plan your stay in Monroe County.

The best time to visit Monroe County and the Florida Keys is November through April, when warm temperatures, lower humidity, and pleasant weather are ideal for beaches, boating, fishing, snorkeling, sightseeing, and island adventures.
Local travel tips for Monroe County

Practical advice for your trip to Monroe County.

  • Plan Your Florida Keys Drive Carefully

    The Overseas Highway (U.S. 1) is the main route connecting the Florida Keys. Allow extra travel time during weekends, holidays, and peak winter season, especially when traveling between Key Largo, Marathon, and Key West.

  • Book Water Activities in Advance

    Popular snorkeling, diving, fishing, and boat tours can fill quickly during peak season. Reserve ahead when possible, and always check local marine and weather conditions before heading onto the water.

Frequently asked questions

Common questions about Monroe County.

What types of vacation rentals are available in Monroe County?

Monroe County vacation rentals include waterfront homes, beach houses, condos, cottages, and island stays throughout the Florida Keys, with options for couples, families, and groups.

Where are the best places to stay in Monroe County?

Popular vacation destinations include Key West, Key Largo, Islamorada, Marathon, and the Lower Keys, each offering different combinations of beaches, boating, fishing, dining, and island attractions.

Are there waterfront vacation rentals in Monroe County?

Yes. Travelers can find waterfront vacation rentals throughout the Florida Keys. Depending on the property, amenities may include private docks, pools, water views, balconies, full kitchens, and boating access.

What are the best things to do in Monroe County?

Popular activities include snorkeling, diving, boating, fishing, kayaking, beach trips, wildlife watching, driving the Overseas Highway, and exploring Key West and other Florida Keys communities.

Why book a Monroe County vacation rental by owner?

Booking a Monroe County vacation rental by owner can provide more space, privacy, kitchens, and home-style amenities. Direct booking may also reduce certain third-party fees, helping travelers find better value for their Florida Keys vacation.

Explore Monroe County vacation rentals by owner in Florida, from waterfront homes and condos to island stays near Key West, beaches, boating, and fishing. Enjoy more space, privacy, and convenient amenities while discovering the Florida Keys. Book directly with property owners and save up to 30%!