Find the best Monroe County Hotels

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

Monroe County Accommodation: Most Popular Cities to Stay

HotelsHotels

Key West

Key West

Check prices for these dates

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Monroe County hotels

Outdoor pool, pool umbrellas, pool loungers
Beachside Resort & Residences

Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
Key West
8.6 out of 10, Excellent, (1813)
"Great stay"
United States
james
The price is 6.286.301 ₫
8.404.287 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Beachside Resort & Residences
2 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town
8.0 out of 10, Very good, (1791)
"Great, friendly staff, nice amenities, easy parking and convenient location "
Canada
Caitlyn
The price is 6.370.861 ₫
8.647.437 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Blue Flamingo Resort Key West
Beach nearby, white sand
Margaritaville Beach House Key West

Margaritaville Beach House Key West

Margaritaville Beach House Key West
4.0 star property
Key West
8.8 out of 10, Excellent, (1773)
" Great location "
United States
Kristen
The price is 9.841.810 ₫
12.781.392 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Margaritaville Beach House Key West
6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
Stock Island
8.8 out of 10, Excellent, (1757)
"The place is great!"
United States
Anna
The price is 6.431.649 ₫
8.847.366 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Oceans Edge Key West Resort, Hotel & Marina
3 outdoor pools, pool umbrellas, pool loungers
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
4.0 star property
Old Town Key West
8.8 out of 10, Excellent, (2936)
"Great Stay!"
United States
mathew
The price is 7.380.305 ₫
10.227.259 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Southernmost Beach Resort and Guesthouses
Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
New Town
8.0 out of 10, Very good, (1168)
"Great location, clean rooms, and great pools!"
United States
Robin
The price is 8.213.438 ₫
9.980.358 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
Key West
8.2 out of 10, Very good, (1007)
"Nice property, comfortable stay - cookies and staff are great!"
United States
David
The price is 6.294.548 ₫
7.969.497 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree Resort by Hilton Grand Key - Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, pool loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1178)
"great place to stay "
United States
michael
The price is 6.825.160 ₫
9.294.309 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
The Perry Hotel & Marina Key West
Fireplace
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.4 out of 10, Very good, (479)
"Clean, great staff and location."
United States
Vincent
The price is 10.499.685 ₫
13.391.045 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Casa Marina Key West, Curio Collection by Hilton
4 outdoor pools, pool umbrellas, pool loungers
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
4.0 star property
Northside Resort
9.0 out of 10, Wonderful, (1204)
"Great place to stay 👌 👍 "
United States
james
The price is 5.122.215 ₫
7.272.447 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Parrot Key Hotel & Villas
Outdoor pool
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1006)
"The room was clean and property was so nice and relaxing. "
United States
Kristen
The price is 10.490.475 ₫
12.985.959 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Beach House, Key West
Outdoor pool, pool loungers
Havana Cabana at Key West

Havana Cabana at Key West

Havana Cabana at Key West
4.0 star property
New Town
8.8 out of 10, Excellent, (1722)
"Enjoyed stay, friendly staff and good shuttle bus"
United States
Abdul
The price is 7.810.506 ₫
10.632.027 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Havana Cabana at Key West
Exterior
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1108)
"Great place "
United States
Oscar
Lime Tree Bay Resort
Outdoor pool
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
Key West
9.6 out of 10, Exceptional, (1006)
"Great staff, hotel and pool."
United States
Lilly
The price is 10.490.475 ₫
12.985.959 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Windward Pointe, Key West
Outdoor pool, pool umbrellas, pool loungers
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (1007)
"Great view, amazing room and friendly staff"
United States
Kristine
The price is 8.609.742 ₫
11.264.861 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
The Reach Key West, Curio Collection by Hilton
Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1600)
"The entire resort was wonderful."
Canada
Mat
The price is 4.974.851 ₫
7.076.893 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Chesapeake Beach Resort
Outdoor pool, pool umbrellas, pool loungers
Hampton Inn Key West FL

Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
Key West
9.0 out of 10, Wonderful, (1293)
"Wonderful stay"
United States
Lindsey
The price is 7.318.202 ₫
8.232.977 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Key West FL
Front of property – evening/night
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1026)
"Our stay was great!"
United States
Richard
The price is 11.025.985 ₫
13.440.650 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Opal Key Resort & Marina, Key West
Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1278)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is 10.499.685 ₫
13.736.693 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Cheeca Lodge & Spa
Outdoor pool, pool cabanas (surcharge), pool umbrellas
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1000)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
The price is 9.026.045 ₫
11.605.046 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Playa Largo Resort & Spa, Autograph Collection
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

Great weekend hotel deals in Monroe County, FL

Showing deals for:2 Jan - 4 Jan

Image gallery for Largo Resort

Outdoor pool, pool umbrellas, pool loungers

Largo Resort

3.0 star property
Key Largo
9.4/10Exceptional (295 reviews)
10% off
Price is 18.107.746 ₫
44.235.778 ₫ total
includes taxes & fees
Largo Resort
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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"This is a great place to stay for family! The balcony was amazing! "
Brandy 3-night trip
Posted 1 day ago
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Absolutely loved this resort and everything was perfect. The 2 bedroom villa as beautiful and the screen in deck was perfect! We will definitely be back! Thank you for making our anniversary great!"
Melinda 5-night trip
Posted 5 days ago
Hyatt Vacation Club at Beach House, Key West

Explore a world of travel with Expedia