Monroe County Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Cities in Monroe County

Top Holiday Rentals Destinations in Monroe County

Our top choices for Monroe County holiday rentals

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (102)
"Unique House boat experience, friendly staff. "
The price is AU$370
includes taxes & fees
2 Sept - 3 Sept
Treasure Harbor

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (521)
"Best kept secret, love staying here,!"
The price is AU$212
includes taxes & fees
10 Sept - 11 Sept
Breezy Palms Resort

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (198)
"We loved our weekend stay here. "
Yacht Haven Marina

Cabins at Bonefish Bay

3.0 star property
9.8 out of 10, Exceptional, (62)
"We stayed in one of the aqua lodges, which is basically a houseboat on the water. It was well equipped and worked nicely for us."
Cabins at Bonefish Bay

Tropical Cottages

3.0 star property
8.6 out of 10, Excellent, (856)
"Wish check in was sooner but made out well, very quiet, personal parking, food truck near by and was all around a good stay"
The price is AU$138
includes taxes & fees
10 Sept - 11 Sept
Tropical Cottages

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is AU$412
includes taxes & fees
8 Sept - 9 Sept
Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (257)
"River boat houses, pool, kayak rentals. "
Old Wooden Bridge Resort and Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (312)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is AU$454
includes taxes & fees
7 Sept - 8 Sept
Hyatt Vacation Club at Sunset Harbor, Key West

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1200)
"Great stay"
Skipjack Resort & Marina

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AU$1,032
includes taxes & fees
4 Sept - 5 Sept
The Islands of Islamorada

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1143)
"Nice roomy accommodations and helpful staff I would stay here again "
The price is AU$150
includes taxes & fees
8 Sept - 9 Sept
Knight's Key Suites

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"Beautiful and peaceful place "
Key Largo Cottages

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (179)
"Very very nice place"
Aqua Lodge Rentals At Coconut Cay

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (50)
"10/10 property and boat was clean. It was perfect for my family with 2 littles. "
Aqua Lodges at 47th Street Gulfside

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (295)
"Really good place to stay "
The price is AU$326
includes taxes & fees
3 Sept - 4 Sept
Anchorage Resort & Yacht Club

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (140)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is AU$359
includes taxes & fees
3 Sept - 4 Sept
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (398)
"Great location. The bike was an awesome way to get around. Pool was very clean and refreshing. "
The price is AU$352
includes taxes & fees
8 Sept - 9 Sept
Steps from Duval, Pool on Site & Bikes Included!

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.8 out of 10, Exceptional, (18)
"Great place will rent again "
The price is AU$361
includes taxes & fees
1 Sept - 2 Sept
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
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.
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

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$138 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

Explore a world of travel with Expedia