A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

Monroe County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Top Cities in Monroe County

A sign for the Key West Museum of Art & History at the Custom House.
Vacation RentalsVacation Rentals

Key West

Key West

Our top choices for Monroe County vacation rentals

A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

1. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (353 reviews)
"Very clean Nice staff"
United States
Doris
The price is CA $226
CA $254 total
includes taxes & fees
Nov 13 - Nov 14
Anchorage Resort & Yacht Club
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $222
CA $495 total
includes taxes & fees
Nov 16 - Nov 17
Aqua Lodges at Hurricane Hole Marina
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (384 reviews)
"Very clean for Florida keys room - no complaints easy check in and out"
United States
Anthony
The price is CA $99
CA $311 total
includes taxes & fees
Dec 4 - Dec 5
Old Wooden Bridge Resort and Marina
A neatly made bed with a grey and white duvet, a wooden headboard, and a bedside table with a lamp and remote control.

4. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,248 reviews)
"We had the pool view..Excellent!"
United States
Brandy
The price is CA $120
CA $166 total
includes taxes & fees
Nov 29 - Nov 30
Knight's Key Suites
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

5. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,298 reviews)
"Nice place"
United States
Gilbert
The price is CA $226
CA $312 total
includes taxes & fees
Nov 15 - Nov 16
Skipjack Resort & Marina
A beach with palm trees, thatched-roof huts, and lounge chairs.

6. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $177
CA $222 total
includes taxes & fees
Nov 15 - Nov 16
Breezy Palms Resort
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

7. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,014 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
The price is CA $140
CA $158 total
includes taxes & fees
Nov 15 - Nov 16
Tropical Cottages
A marina with several docked boats and a row of small, white cabins with blue roofs.

8. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (385 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is CA $166
CA $386 total
includes taxes & fees
Dec 1 - Dec 2
Yacht Haven Marina
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

9. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (184 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is CA $169
CA $389 total
includes taxes & fees
Nov 17 - Nov 18
Treasure Harbor
A beach with palm trees, a sandy path, and beach chairs.

10. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (239 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is CA $131
CA $362 total
includes taxes & fees
Nov 15 - Nov 16
Aqua Lodge Rentals At Coconut Cay
A pool area with a wooden deck, lounge chairs, and a waterfall feature.

11. Lighthouse Suites Collection

Lighthouse Suites Collection
3.5 star property
Old Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
United States
Melissa
The price is CA $735
CA $1,068 total
includes taxes & fees
Nov 13 - Nov 14
Lighthouse Suites Collection
A beachside resort with a wooden deck, palm trees, and a sunset view.

12. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is CA $552
CA $966 total
includes taxes & fees
Nov 15 - Nov 16
Grand Marina Suite by Brightwild Waterfront
A resort with a swimming pool, lounge chairs, and a view of the ocean.

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is CA $244
CA $314 total
includes taxes & fees
Dec 13 - Dec 14
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A beach with thatched umbrellas, lounge chairs, and a clear view of the ocean.

14. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (42 reviews)
"It was very nice!!"
United States
Michelle
The price is CA $423
CA $476 total
includes taxes & fees
Dec 12 - Dec 13
Kings Kamp
Exterior

15. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (61 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is CA $203
CA $428 total
includes taxes & fees
Nov 15 - Nov 16
Aqua Lodges at 47th Street Gulfside
A modern house with a swimming pool, a balcony, and a well-maintained garden.

16. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is CA $1,170
CA $1,884 total
includes taxes & fees
Nov 19 - Nov 20
Contra House Key West
A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

17. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
The price is CA $1,156
CA $1,300 total
includes taxes & fees
Nov 15 - Nov 16
Premium Floating Bungalow by Stay Ombi
Property grounds

18. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
The price is CA $243
CA $535 total
includes taxes & fees
Dec 1 - Dec 2
Piece of Paradise
A beachside area with thatched umbrellas, picnic tables, and chairs.

19. Walk to Beach: Florida Keys Gem w/ Ocean Views

Walk to Beach: Florida Keys Gem w/ Ocean Views
3.0 star property
Long Key
The price is CA $732
CA $1,019 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Beach: Florida Keys Gem w/ Ocean Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

20. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is CA $734
CA $1,385 total
includes taxes & fees
Nov 15 - Nov 16
Atlantic View Luxury Villa with 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monroe County Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The office attendant was super nice"
Laurie 1-night trip
Posted less than an hour ago
Chesapeake Beach Resort

Find out more about Monroe County

Everything you need to know about Monroe County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monroe County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Monroe County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monroe County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monroe County vacation rentals we have selected for you start as low as CA $158 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 vacation 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 vacation.

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.