Monroe County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Top Cities in Monroe County

Our top choices for Monroe County holiday rentals

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (138 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
The price is AU$475
includes taxes & fees
9 Mar - 10 Mar
Treasure Harbor

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (308 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
Old Wooden Bridge Resort and Marina

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (279 reviews)
"Very clean and great staff. "
United States
Barbara
Yacht Haven Marina

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (626 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is AU$350
includes taxes & fees
25 Mar - 26 Mar
Breezy Palms Resort

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (210 reviews)
"Room was clean, staff was friendly, view from deck was amazing, took the free kayaks out and saw a Manatee, convenient location. Great experience!"
United States
Wendy
Aqua Lodge Rentals At Coconut Cay

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,178 reviews)
"Very a nice place clean nice location good price"
United States
Pawel
The price is AU$339
includes taxes & fees
5 Apr - 6 Apr
Knight's Key Suites

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,234 reviews)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.6 out of 10, Excellent, (316 reviews)
"Quaint and very convenient. Beautiful views of the marina and water. Staff was very helpful and recommended a great restaurant. "
United States
Michelle
The price is AU$400
includes taxes & fees
8 Mar - 9 Mar
Anchorage Resort & Yacht Club

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (181 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is AU$539
includes taxes & fees
29 Mar - 30 Mar
Aqua Lodges at Hurricane Hole Marina

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (53 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is AU$643
includes taxes & fees
12 Mar - 13 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (44 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is AU$593
includes taxes & fees
17 Mar - 18 Mar
Amazing Ocean view condo

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (112 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is AU$741
includes taxes & fees
6 Apr - 7 Apr
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (42 reviews)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
The price is AU$681
includes taxes & fees
9 Mar - 10 Mar
Ocean view condo with balcony/marina view

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
The price is AU$767
includes taxes & fees
23 Mar - 24 Mar
3212 Across from Pool * King & Queen/Twin Bunk Bed

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (27 reviews)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is AU$739
includes taxes & fees
11 Mar - 12 Mar
Lazy Daze Double King Suite Ocean Pointe 2310

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (150 reviews)
"Enjoyed the area. Not to far from Key West but far enough there wasn't a crowd"
United States
Donna P.
The price is AU$617
includes taxes & fees
14 Mar - 15 Mar
Quaint cottage, pool, dockage just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is AU$504
includes taxes & fees
12 Mar - 13 Mar
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (162 reviews)
"Very clean and quiet location. Beds were comfy and all necessities were provided. Would definately recommend!"
United States
Arielle F.
The price is AU$753
includes taxes & fees
23 Mar - 24 Mar
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is AU$639
includes taxes & fees
12 Mar - 13 Mar
Waterfront Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Monroe County Hotel Reviews

Find out more about Monroe County

Everything you need to know about Monroe County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monroe County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monroe County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Monroe County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monroe County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monroe County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Monroe County holiday rentals we have chosen for you start as low as AU$336 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Monroe County rentals

At Expedia, we put the best Monroe County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Monroe County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monroe County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monroe County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia