Holiday Rentals in Monroe County

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Holiday RentalsHoliday Rentals

Key West

Key West

Our top choices for Monroe County holiday rentals

25-inch flat-screen TV with digital channels, TV
Treasure Harbor

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (117)
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor
Marina
Skipjack Resort & Marina

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1216)
"Beautiful location clean rooms friendly staff "
United States
Tiffany
Skipjack Resort & Marina
42-inch Smart TV with digital channels, Netflix, Hulu
Yacht Haven Marina

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (234)
"Nice Lodge nice area close to grocery store & shops, will love to stay there again."
United States
Xiomeidy
Yacht Haven Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (278)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €259
includes taxes & fees
17 Dec - 18 Dec
Aqua Lodges at Hurricane Hole Marina
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (586)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is €128
includes taxes & fees
17 Dec - 18 Dec
Breezy Palms Resort
Exterior
Tropical Cottages

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (908)
"Beautiful place, conveniently located "
United States
Clifton
The price is €96
includes taxes & fees
17 Dec - 18 Dec
Tropical Cottages
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (321)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is €287
includes taxes & fees
18 Dec - 19 Dec
Hyatt Vacation Club at Sunset Harbor, Key West
Premium bedding, soundproofing, iron/ironing board, free WiFi
Knight's Key Suites

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1157)
"Very good location.. Clean room."
United States
Leonor
The price is €98
includes taxes & fees
17 Dec - 18 Dec
Knight's Key Suites
Deluxe Bungalow | Terrace/patio
Cabins at Bonefish Bay

Cabins at Bonefish Bay

Cabins at Bonefish Bay
3.0 star property
Marathon
9.6 out of 10, Exceptional, (83)
"The cabin was clean and new. I liked that it was right on the water and in a great location to explore the Keys"
United States
Kieran
Cabins at Bonefish Bay
Apartment
Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
Ocean Front One Bedroom Residence
BBQ/picnic Area
Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (198)
"Kitchen was very well equipped and the property was very pet friendly. "
United States
Tomas
Aqua Lodge Rentals At Coconut Cay
Apartment
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is €368
includes taxes & fees
18 Dec - 19 Dec
Island View 1BR Residence With Balcony
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (69)
"Great for family vacation with kids. love it"
United States
Dixania
The price is €621
includes taxes & fees
17 Dec - 18 Dec
The Islands of Islamorada
Apartment
Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is €465
includes taxes & fees
17 Dec - 18 Dec
Ocean Front 1BR Suite With Direct Beach Access
Exterior
Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.6 out of 10, Excellent, (297)
"Really good place to stay "
United States
Elier
The price is €216
includes taxes & fees
17 Dec - 18 Dec
Anchorage Resort & Yacht Club
Exterior
Steps from Duval, Pool on Site & Bikes Included!

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, (413)
"Everything was excellent!"
United States
Susan L.
The price is €338
includes taxes & fees
14 Jan - 15 Jan 2026
Steps from Duval, Pool on Site & Bikes Included!
Fishing
Kings Kamp

Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.8 out of 10, Excellent, (23)
"Kings Kamp was a charming stay. The owners were friendly and made the stay easy"
United States
Erica
Kings Kamp
Meeting facility
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
Key West
8.2 out of 10, Very good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Old Town Key West
10.0 out of 10, Exceptional, (27)
"Clean room, amazing location, the host was very communicative and helpful. They had a car service ready to pick us up at the airport which was phenomenal. "
United States
Lauren S.
The price is €327
includes taxes & fees
17 Dec - 18 Dec
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"Beautiful property that cant be described in words. The staff was welcoming and very helpful. I honestly did not want to leave. "
ShaBrima 3-night trip
Posted 12 hours ago
Margaritaville Beach House Key West

Find out more about Monroe County

Holiday Homes in Monroe County

Search for holiday homes in Monroe County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Monroe County using one of the methods below: 

  • View our selection of featured holiday homes in Monroe County
  • Use the map to find apartments and other holiday rentals in the Monroe County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Monroe County while they last

Look no further and take a look at our great range of rental properties in Monroe County!