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

Monroe County Vacation Rentals

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Top Cities in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.
Vacation RentalsVacation Rentals

Key West

Key West

Our top choices for Monroe County vacation rentals

A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is CA $97
CA $181 total
includes taxes & fees
Nov 17 - Nov 18
Breezy Palms Resort
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

2. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,244 reviews)
"We had the pool view..Excellent!"
United States
Brandy
The price is CA $127
CA $173 total
includes taxes & fees
Nov 29 - Nov 30
Knight's Key Suites
A row of floating houses with balconies, connected by walkways, on calm water.

3. 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 $138
CA $394 total
includes taxes & fees
Nov 4 - Nov 5
Aqua Lodges at Hurricane Hole Marina
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

4. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,013 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 $133
CA $149 total
includes taxes & fees
Nov 4 - Nov 5
Tropical Cottages
A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

5. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (352 reviews)
"Very nice room"
United States
Sabrina
The price is CA $222
CA $250 total
includes taxes & fees
Nov 4 - Nov 5
Anchorage Resort & Yacht Club
A spacious living area with a gray sectional sofa, wooden beams, and a ceiling fan.

6. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (238 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is CA $118
CA $342 total
includes taxes & fees
Nov 4 - Nov 5
Aqua Lodge Rentals At Coconut Cay
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

7. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (180 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 $150
CA $365 total
includes taxes & fees
Nov 4 - Nov 5
Treasure Harbor
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

8. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (379 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is CA $162
CA $379 total
includes taxes & fees
Nov 5 - Nov 6
Old Wooden Bridge Resort and Marina
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

9. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,296 reviews)
"Great spot"
Canada
Justin
The price is CA $222
CA $307 total
includes taxes & fees
Nov 4 - Nov 5
Skipjack Resort & Marina
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

10. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (380 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
The price is CA $133
CA $347 total
includes taxes & fees
Nov 4 - Nov 5
Yacht Haven Marina
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

11. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is CA $188
CA $522 total
includes taxes & fees
Nov 16 - Nov 17
Florida Keys Getaway - Slps 4 - Ocean View
A white building with a covered porch and a palm tree.

12. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
The price is CA $162
CA $366 total
includes taxes & fees
Nov 18 - Nov 19
Steps from Duval, Pool on Site & Bikes Included!
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 $248
CA $319 total
includes taxes & fees
Dec 2 - Dec 3
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Exterior

14. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
The price is CA $239
CA $527 total
includes taxes & fees
Dec 2 - Dec 3
Piece of Paradise
A wooden deck with a large tree, outdoor seating, and a marina in the background.

15. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is CA $233
CA $392 total
includes taxes & fees
Nov 9 - Nov 10
Poolside Cottage #412
A small, private entrance to a house with a brick pathway leading to a door.

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (40 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
The price is CA $191
CA $513 total
includes taxes & fees
Nov 17 - Nov 18
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

17. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay"
United States
walter l.
The price is CA $232
CA $505 total
includes taxes & fees
Nov 10 - Nov 11
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Exterior

18. 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 $184
CA $403 total
includes taxes & fees
Nov 19 - Nov 20
Aqua Lodges at 47th Street Gulfside
A tropical garden pathway leading to a building with a yellow facade and green shutters.

19. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
The price is CA $232
CA $505 total
includes taxes & fees
Dec 1 - Dec 2
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

20. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $182
CA $515 total
includes taxes & fees
Nov 19 - Nov 20
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Great stay! Would visit again."
Chanele 3-night trip
Posted less than an hour ago
Parrot Key Hotel & Villas

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 $149 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.