Discover a selection of 97 holiday rentals in Monroe County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 136 per night, and houses and flats & apartments are popular options for a stay in Monroe County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Monroe County
Destination guide

Find the perfect holiday rental for your Monroe County getaway

Learn about the unique charm of Monroe County with a stay in a holiday home rental. This city has something for everyone. Duval Street and Smathers Beach are just a couple of the must-see attractions. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Things to do

Activities and attractions in and around Monroe County

Are you hoping to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Monroe County a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (2.1 mi / 3.4 km)
  • Key West Visitors Center (28 mi / 45 km)
  • The Kite House (1.7 mi / 2.7 km)
  • MLK Community Pool & Community Center (2 mi / 3.2 km)
  • Blue Hole (26.7 mi / 42.9 km)
Natural features

Exploring the natural features in Monroe County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Monroe County is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Smathers Beach (0.8 mi / 1.4 km)
  • Higgs Beach (1.3 mi / 2.1 km)
  • Key West Tropical Forest and Botanical Garden (1.6 mi / 2.7 km)
  • South Beach (1.8 mi / 2.9 km)
  • Key West Butterfly and Nature Conservatory (1.8 mi / 3 km)
  • Southernmost Point (1.9 mi / 3.1 km)
How to get there

Travelling to and around Monroe County

The nearest airport is in Key West, FL (EYW-Key West Intl.), located 1.3 mi (2 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 46.6 mi (75 km) away.

What are the top holiday rentals in Monroe County?

Whether you're planning an adventurous break with friends or a romantic rendezvous with your sweetheart, one of these top holiday rentals in Monroe County is sure to catch your eye:

  • "Sombrero Beach Home On Canal With Private Dock And Heated Pool": This Marathon property offers 3 bedrooms and is highly rated among guests. Conveniences such as a washing machine and a living room help make your stay a memorable one.
  • "Key West Oasis, Seperate Cottage": Located in Key West Historic District, this popular getaway has 2 bedrooms and plenty of handy amenities. Golf and off-street parking options are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Monroe County holiday rental for you.

What are the best tiny house holiday rentals in Monroe County?

For a different kind of holiday experience, book one of Vrbo's tiny house rentals in Monroe County. A word of warning though — after you've experienced the tiny house lifestyle, the temptation to downsize and move into one of these miniature digs will be hard to resist!

  • Get ready for a simpler way of living at "New Tiny House - Introductory Price Minutes From Sanibel And Fort Myers Beach". Amenities at this tiny house in Iona include shopping, coffee and tea making facilities and more.
  • Alternatively, book a weekend at "Private Pool Tiny Home With Resort Feel". Located in Boynton Beach, this tiny abode comes with shopping and a blender.

What are the top-rated holiday rentals for weekend getaways in Monroe County?

Short on time but want a change of scene? A weekend break is just what the doctor ordered. Snap up one of these excellent rental properties and get ready for good food, sleep-ins and relaxation:

  • "Kayak Boot Key Harbour, 75ft Canal Home" - Located in Marathon, this getaway offers its guests handy extras including an iron and ironing board and a fridge.
  • "Wow Private Pool, Ocean Front" - This is another option offering all the things that make up a fab weekend away. Expect a beach and a fridge at this Marathon property.

Can I find studio apartments for rent in Monroe County?

Forget about the tired old hotel and lock in one of our studio apartments in Monroe County. Here's where you can relax in your own pad and experience your next travel destination like a local:

  • "Waterfront Luxury Living Inside And Out" in Marathon squeezes loads of convenient amenities into its single room space, such as a smart TV and a porch.
  • Begin your day with a hot coffee and a cooked breakfast at "Ocean Front 1/1, Amazing Ocean". This Tavernier retreat has all the essentials to make your stay cosy, including beach towels and a beach.

Can I find short term rentals in Monroe County?

With Vrbo's terrific range of short-term rentals in Monroe County, you're bound to find a place to suit your needs. Whether you're on the lookout for somewhere to relax on your own or to get together with the family, these options are difficult to beat:

  • Base yourself close to central Marathon and spend your days visiting the area's top sights from "Kayak Boot Key Harbour, 75ft Canal Home". Along with its convenient location, this retreat has everything you need to make your holiday comfortable and relaxed.
  • Another popular option is "Wow Private Pool, Ocean Front" in Marathon. Whether you're on a quick stopover or enjoying a couple of days away, this comfortable holiday rental will make you feel right at home.

What are the best romantic weekend getaways in Monroe County?

Whether you've been with each other for a few months, a decade or an eternity, nothing beats a romantic weekend getaway to keep passions alive. If you're looking for someplace idyllic to spend a couple of days with your sweetheart, you'll be wooed by these retreats:

  • Channel your inner Casanova at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". This Marathon stay is custom-made for romance, with amenities like a restaurant dining guide and air conditioning to help set the mood.
  • Alternatively, spend a few days sipping Champagne and cuddling up at "Key West Oasis, Seperate Cottage". Beauty services and a swimming pool add to the dreamy atmosphere of this Key West Historic District property.

Are there mansions for rent in Monroe County?

Forget queuing up at the hotel breakfast bar or trying to find a chaise lounge around the pool during your holiday. Rally your favourite people and give your getaway a major upgrade with one of these mansions for rent in Monroe County:

  • Settle in and make the most of all the awesome things on offer at "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" in Old Town Key West. Top amenities here include a swimming pool and golf.
  • With beauty services and a swimming pool among its many highlights, "Mediterranean Mansion In Florida Keys" also promises to make your holiday an unforgettable one. This palatial pad is located in Key Largo.

What's the best place to stay if you're looking to rent a house for a weekend in Monroe County?

Key West. How come? This laid-back area in Monroe County is home to Smathers Beach. When you're not getting your fix of R&R at your holiday rental beside the water, meander along the beach's white sand, search for washed-up treasures and soak up palm trees views. If there's a better way to spend a weekend with the family, it doesn't exist yet.

What are the best large group holiday rentals in Monroe County?

When it comes to who you take on holiday, we think the more people the merrier. If you're searching for a getaway with plenty of space to fit your entire crew, one of these large group holiday rentals in Monroe County might be just the ticket:

  • "New Photos: Drive To Your Getaway": With 5 bedrooms, this top option in Key West Historic District has more than enough room for the whole gang. Amenities like a swimming pool and a beach view will keep everyone happy.
  • "Spectacular Waterfront Estate": You'll get your team's tick of approval at this option in Marathon which comes with a garden, a swimming pool and more. It has 6 bedrooms that will comfortably accommodate any large group.

Are there large holiday rentals that sleep 30 or more in Monroe County?

If you're planning to host a big family escape or a special event in Monroe County, you won't have to worry about leaving anyone off your invite list. We've got an excellent range of large holiday rentals that will fit as many people as you like. Here are some great examples:

  • "All Together Now @ Old Town Three Homes And Pools + Last Key Services": With 13 bedrooms sleeping up to 32 people, this holiday rental in Downtown Key West has all the space you need. A swimming pool and a nearby marina are just some of the amenities available here.
  • "Moosybärhütte, Gruppenunterkunft Für Bis Zu 31 Personen": Everyone can join the fun at this retreat in Bahama Village. It has 5 bedrooms and sleeps up to 31 guests. Top amenities here include a swimming pool and a garden.

Explore destinations around Monroe County

Key West
1,915 holiday rentals
Key Largo
1,328 holiday rentals
1,373 holiday rentals
1,308 holiday rentals
Key Colony Beach
1,345 holiday rentals
1,273 holiday rentals
Cudjoe Key
455 holiday rentals
Little Torch Key
386 holiday rentals
Sugarloaf Key
1,005 holiday rentals
Summerland Key
433 holiday rentals
Marathon Shores
1,100 holiday rentals
Big Pine Key
411 holiday rentals
Lower Sugarloaf Key
323 holiday rentals
Ramrod Key
296 holiday rentals
Key West Naval Station
2,151 holiday rentals
Big Torch Key
432 holiday rentals
Duval Street
1,860 holiday rentals
Middle Torch Key
423 holiday rentals
Upper Sugarloaf Key
381 holiday rentals