Vacation Rentals in Monroe County

Start comparing over 4,486 rentals in Monroe County and book at the best price!

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8.0

Vacation Rentals in Monroe County

Vacation rental for 4 people, with balcony and balcony/terrace as well as lake view

2 bedrooms

from $539 / nightFREE cancellation

Vacation rental for 4 people, with terrace

1 bedroom

7.5

(14 reviews)

from $347 / night

Vacation rental for 2 people, with terrace and yard

1 bedroom

9.6

(95 reviews)

from $129 / nightFREE cancellation

Vacation rental for 6 people, with pool and yard

2 bedrooms

from $195 / nightFREE cancellation

Vacation rentals with free cancellation

Vacation rental for 4 people, with pool

2 bedrooms

9.2

(47 reviews)

from $209 / nightFREE cancellation

Vacation rental for 4 people, with balcony/terrace

2 bedrooms

9.6

(32 reviews)

from $351 / nightFREE cancellation

Vacation rental for 2 people, with terrace and yard, with pets

10.0

(90 reviews)

from $265 / nightFREE cancellation

Vacation rental for 2 people, with pool and yard as well as terrace

1 bedroom

9.3

(41 reviews)

from $331 / nightFREE cancellation

Vacation rentals with sea view

Sea view

Vacation rental for 12 people, with view and yard as well as ocean view

4 bedrooms

10.0

(3 reviews)

from $675 / nightFREE cancellation

Sea view

Vacation rental for 8 people, with balcony and pool, with pets

4 bedrooms

from $1,855 / nightFREE cancellation

Sea view

Vacation rental for 8 people, kid friendly

3 bedrooms

9.8

(10 reviews)

from $758 / nightFREE cancellation

Sea view

Vacation rental for 10 people, with pool and yard as well as balcony, kid friendly

4 bedrooms

from $286 / nightFREE cancellation

Vacation rentals with pets allowed

Pets allowed

Vacation rental for 2 people, with terrace, with pets

1 bedroom

7.6

(51 reviews)

from $177 / nightFREE cancellation

Pets allowed

Mobile home for 6 people, with pool and hot tub, with pets

10.0

(3 reviews)

from $192 / nightFREE cancellation

Pets allowed

Vacation rental for 4 people, with yard and terrace

2 bedrooms

8.4

(90 reviews)

from $209 / nightFREE cancellation

Pets allowed

Vacation rental for 4 people, with hot tub and terrace

2 bedrooms

8.5

(15 reviews)

from $511 / nightFREE cancellation

Vacation Rentals with Pool

Pool

Vacation rental for 2 people, with terrace

1 bedroom

9.2

(17 reviews)

from $370 / nightFREE cancellation

Pool

Mobile home for 2 people, with hot tub and terrace as well as pool

2 bedrooms

10.0

(26 reviews)

from $194 / nightFREE cancellation

Pool

Vacation rental for 4 people, with hot tub and pool as well as terrace

9.5

(22 reviews)

from $283 / nightFREE cancellation

Pool

Vacation rental for 6 people, with hot tub and balcony as well as pool

2 bedrooms

9.5

(76 reviews)

from $274 / nightFREE cancellation

Find Vacation Rentals in Monroe County

Popular Destinations in Monroe County

Best Vacation Rentals in Monroe County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Vacation Rental for 2 Guests in Cudjoe Key, Lower Keys

Vacation Rental for 2 Guests in Cudjoe Key, Lower Keys, Picture 1

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Vacation Rental for 2 Guests in Cudjoe Key, Lower Keys, Picture 3

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Cudjoe Key, Lower Keys

Vacation Rental • 388 ft² • 1 Bedroom

Cudjoe Key, Lower Keys

8.6

(149 reviews)

Cottage #3 - Quaint, clean, comfortable cottage just 20 miles from Key West. Located on the oceanfront. Cottage offers a full kitchen, screened patio, a single bedroom with a queen bed. This cottage is only steps away from our pool. The dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Cottages to be your Home Away From Home.

from $172 / night

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Cudjoe Key, Lower Keys

Vacation Rental • 388 ft² • 1 Bedroom

Cudjoe Key, Lower Keys

8.5

(69 reviews)

Cottage #2 - Charming and serene, clean, comfortable cottage just 20 miles from Key West. Located adjacent to the pool. Cottage offers a full kitchen, screened patio, a single bedroom with a queen bed. This cottage is situated only steps away from our pool. The dock, seawalls are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Cottage to be your Home Away From Home.

from $183 / night

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Vacation Rental for 4 Guests in Key West, Lower Keys

Vacation Rental for 4 Guests in Key West, Lower Keys, Picture 1

Vacation Rental for 4 Guests in Key West, Lower Keys, Picture 2

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Key West, Lower Keys

Vacation Rental • 420 ft² • 1 Bedroom

Key West, Lower Keys

9.3

(3 reviews)

A QUIET BUNGALOW IN THE HISTORIC SEAPORT...Private one bedroom home in the heart of Old Town. A great place for a couple's getaway where you can live like a local. Located in a serene setting off the main streets and surrounded by other "cigar" cottages. A shared, heated, community pool is a great place to cool off or sit and enjoy a cocktail.***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEFURNISHINGS...Newly decorated throughout with the feel of home. Nicely equipped kitchen to cook your favorite meals. There is a high top table with storage for wine glasses galore so our wine lover won't...

from $138 / night

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Popular Destinations in Monroe County

Cudjoe KeyExplore destination →

Prices and availability

Current Vacation rental prices Monroe County

$560for 3 Aug - 10 Aug

$583 annual average

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Average price per week

Current vacation rental availability Monroe County

19%for 3 Aug - 10 Aug

38% annual average

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Percentage of available rentals

FAQs: Vacation Rentals in Monroe County

How much did it cost for a vacation rental in Monroe County last year?

At an average cost of $494 per night, Monroe County lies at the upper end of the price range for vacation rentals in the USA.

During which months are vacation rentals cheaper in Monroe County?

]If you want to get the most out of your money, the most affordable months to visit Monroe County are September ($434 the average per night for accommodation), August ($456), and June ($457).

When are vacation rentals more expensive in Monroe County?

Analyzing the data from last year, we found that costs per night for accommodation here are usually higher, on average, during the months of February ($591), March ($562), and January ($532).

Should I plan a trip to Monroe County well in advance?

So you don't run out of accommodation options in Monroe County, we recommend you to be proactive as 75% of rentals are usually booked, according to last year's data.

What are the best months for a spontaneous getaway?

The months when it's easiest to find available accommodation in Monroe County are May (the average amount of properties that are available reached 93% of the total last year), June (80%), and August (27%).