Find Vacation Homes in Monroe County, FL from $363

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Top Cities in Monroe County

Vacation Homes in Monroe County

Vacation Home in Marathon

2.5 star property
9.0 out of 10, Wonderful, (111)
"It was my first time staying there but it won’t be my last."
United States
Dennis
The Hammocks at Marathon

Vacation Home in Old Town Key West

7.0 out of 10, Good, (2)
"So quaint and private. Close to everything and the private pool was absolutely lovely! Owners were accommodating and so friendly and nice!"
United States
Sandi H.
Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Vacation Home in Sands

$545 nightly
The price is $604
Dec 2 - Dec 3
Total with taxes and fees
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Vacation Home in Marathon

9.8 out of 10, Exceptional, (49)
"Beautiful house, wonderful location. "
United States
Melissa S.
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Vacation Home in Beachside

2.0 star property
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

Vacation Home in Duck Key

9.2 out of 10, Wonderful, (90)
"Great place"
United States
Diego
Restful waterfront townhome with deck, great water views & washer/dryer

Vacation Home in Marathon

10.0 out of 10, Exceptional, (73)
"Loved the location and this home was the perfect place to spend a week with the family!! "
United States
Diana W.
Outstanding pool and outdoor area 5 minute walk to beach!

Vacation Home in Duck Key

9.4 out of 10, Exceptional, (9)
"Everything about the house was amazing. It was cozy, comfortable and extremely nice and clean! Can’t wait to come back!"
United States
Candice L.
Charming townhome with ocean views, an open porch & steps from the water

Vacation Home in Key West Historic District

10.0 out of 10, Exceptional, (35)
"Great updated house in the perfect location. Super easy communication with the host, who were very accommodating to our needs in the trip. Would definitely stay here again!"
United States
Mike D.
$927 nightly
The price is $1,002
Dec 7 - Dec 8
Total with taxes and fees
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Vacation Home in Coral Lagoon

9.8 out of 10, Exceptional, (101)
"Great place for the entire family! Will definitely book again. "
United States
Kyle C.
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Vacation Home in Old Town Key West

9.6 out of 10, Exceptional, (193)
"Perfect stay, awesome communication with the property manager at all times 5"
United States
Devotion808 g.
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

Vacation Home in Old Town Key West

10.0 out of 10, Exceptional, (194)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
$1,587 nightly
The price is $1,762
Dec 3 - Dec 4
Total with taxes and fees
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Vacation Home in Marathon

9.8 out of 10, Exceptional, (9)
"Very clean and pleasant property. The driveway was large enough for our truck and boat, which was extremely helpful when we were coming and going. The owner was easy to communicate with. We enjoyed our trip!"
United States
Kathleen T.
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

Vacation Home in Old Town Key West

9.6 out of 10, Exceptional, (95)
"The house has a great location and the staff was very attentive. Would stay here again!! Thank you!! "
United States
Ellen M.
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

Vacation Home in Stock Island

9.8 out of 10, Exceptional, (96)
"This place is perfect for a family vacation! The rooms are beautiful and the beds are so comfy. Also, the back decks are a great place to hang out. Really enjoyed our stay!"
United States
Veronica S.
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Vacation Home in Key Largo

9.6 out of 10, Exceptional, (81)
"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"
United States
Brad W.
$326 nightly
The price is $363
Dec 1 - Dec 2
Total with taxes and fees
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Vacation Home in Silver Shores

9.6 out of 10, Exceptional, (106)
"Property was great. Everyone enjoyed their stay definitely would come back."
United States
Bradley P.
BEACHFRONT POOL HOME

Vacation Home in Duck Key

9.4 out of 10, Exceptional, (26)
"My vacation at Harbor Village in the keys was fantastic the house was clean and spacious for the 7 of us"
United States
Michele S.
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Vacation Home in Summerland Key

8.2 out of 10, Very Good, (98)
"Thank you so much for the great stay! The ocean view was beautiful! The landscaping with surrounding trees and flowers was lovely! The house was comfortable and had everything that we needed. It was perfect for our family!"
United States
Deidra B.
Private Secluded Ocean View & Pool Near Key West

Vacation Home in Marathon

10.0 out of 10, Exceptional, (75)
"Being close to sombrero beach was our goal. The house itself was so perfect we barely left. Great stay"
United States
Timothy G.
FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~
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.

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Top Monroe County Hotel Reviews

Price trends for hotels in Monroe County

Less expensive
More expensive
Next month
September
February
$518
Month
Price
January
$611
February
$724
March
$723
April
$518
May
$471
June
$472
July
$390
August
$392
September
$385
October
$457
November
$427
December
$518
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Monroe County. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Monroe County

Booking Tips to Find the Best Monroe County Vacation Homes


How much does it cost to rent a vacation home in Monroe County?

You can find incredible Monroe County vacation homes for all types of budgets: between $363 and $1,762 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Monroe County?

If you are looking for a great deal on your vacation home in Monroe County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Monroe County?

There are 3860 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Monroe County?

Begin by entering your trip dates to see what type of Monroe County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Monroe County?

Booking Monroe County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Monroe County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Monroe County along with your vacation property, into a Monroe County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Monroe County Vacation Homes information

Number of reviews
1,287
Accommodation
3860 Vacation Homes
Lowest Price
$363
Highest Price
$1,762

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