Find Vacation Homes in Monroe County, FL from $308

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Top Cities in Monroe County

Vacation Homes in Monroe County

The Hammocks at Marathon
2.5 star property
9.0 out of 10, Wonderful, (109)
"We arrived early but were able to use the pool. Lovely cannon firing ceremony at sunset with a sunset shot from the bar. We ate wings and a pretzel from the bar which were both delicious. Room was large and the bed was really comfortable."
United Kingdom
Janet
The Hammocks at Marathon
Tropical Key West out of the way
9.6 out of 10, Exceptional, (178)
"The location was close to our diving spot and not far from all the sites. The host was awesome. Very responsive and made us feel very welcome. "
United States
Dianne M.
Tropical Key West out of the way
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
9.8 out of 10, Exceptional, (49)
"We have stayed here a few times. Have another trip booked already. Property manager Monica was extremely pleasant and easy to work with."
United States
tracy b.
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Perfect Location, Private Heated Pool, Pristine Luxury Home!
10.0 out of 10, Exceptional, (192)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
$1,586 nightly
The price is $1,761
Nov 10 - Nov 11
Total with taxes and fees
Perfect Location, Private Heated Pool, Pristine Luxury Home!
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
10.0 out of 10, Exceptional, (210)
"Absolutely amazing stay for our annual guys trip. Location is great, the place was spotless, and finding a place with with a pool just off of Duval located on this side of Duval is a true gem. The property service did an amazing job with communication. "
United States
Brandon D.
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
2.5 star property
9.6 out of 10, Exceptional, (15)
"Great place to stay. Great location and super clean."
United States
James G.
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Restful waterfront townhome with deck, great water views & washer/dryer
9.2 out of 10, Wonderful, (88)
"Great place"
United States
Diego
Restful waterfront townhome with deck, great water views & washer/dryer
Charming townhome with ocean views, an open porch & steps from the water
9.4 out of 10, Exceptional, (8)
"This place is nice, and it's clean. It was great for what we needed for our quick dive trip to Marathon. We did reach out to management for extra linens and we did not receive them. It is managed by a larger company, so if you are looking for a little bit more of a personal touch this might not be the best place. But overall it is a very nice place to stay."
United States
Olivia T.
Charming townhome with ocean views, an open porch & steps from the water
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (229)
"My mom and I were absolutely amazed by the property, we loved everything and hope to come back again!"
United States
Emma T.
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
8.8 out of 10, Excellent, (196)
"We stayed here for Fantasy Fest and loved it. It was the perfect walking distance to everything and the historic charm of this cottage was perfect."
United States
Michael M.
$600 nightly
The price is $667
Nov 18 - Nov 19
Total with taxes and fees
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.6 out of 10, Exceptional, (84)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
$621 nightly
The price is $690
Nov 19 - Nov 20
Total with taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
9.6 out of 10, Exceptional, (43)
"This is the second time we stay in this property in less than a year and we couldn’t been happier. It is clean, spacious; it has all you need and location is great!. Host is very responsive and accomodaring. We cannot wait to come back hopefully before the end of the year. "
United States
MAIDELIS F.
$278 nightly
The price is $308
Dec 1 - Dec 2
Total with taxes and fees
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
9.6 out of 10, Exceptional, (25)
"Loved our stay!"
United States
Jessica B.
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (45)
"Loved it! The view is unbelievable! Such a such place and tastefully decorated. Beds were comfy and it had just what we needed to cook. Nice big table to play games. We will definitely book again! "
United States
Jennifer B.
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
9.8 out of 10, Exceptional, (80)
"Incredible Stay! "
United States
Jill Z.
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Waterfront escape with stunning views, private balconies, near attractions
8.6 out of 10, Excellent, (9)
"This property is spacious and the set up inside is great with a full bedroom and bathroom downstairs and 2 more full bedrooms and bathrooms upstairs. The location along the dock is amazing with a large shade tree to make the afternoons and evenings cool. We really enjoyed the large outdoor table and chairs. We had a great vacation and will definitely be back!"
United States
Stephanie T.
Waterfront escape with stunning views, private balconies, near attractions
Cudjoe Cottages, swimming pool, just 20 miles from Key West
8.8 out of 10, Excellent, (147)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
United States
Charles V.
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Kingfish Keep | Lively Escape on Duval! Balcony!
9.8 out of 10, Exceptional, (20)
"Awesome location with excellent communication. "
United States
Gary W.
$359 nightly
The price is $395
Nov 16 - Nov 17
Total with taxes and fees
Kingfish Keep | Lively Escape on Duval! Balcony!
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
9.6 out of 10, Exceptional, (214)
"Wonderful stay here for our family. Great price and close to Key West!"
United States
Donnette D.
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
10.0 out of 10, Exceptional, (4)
"Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience "
United States
Debbie W.
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
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
This month
Next month
September
February
$483
$545
Month
Price
January
$592
February
$712
March
$695
April
$547
May
$516
June
$448
July
$522
August
$414
September
$392
October
$597
November
$483
December
$545
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 $308 and $1,761 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
1,652
Accommodation
3860 Vacation Homes
Lowest Price
$308
Highest Price
$1,761

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