Vacation Homes in Monroe County

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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Top Cities in Monroe County

Vacation HomesVacation Homes

Key West

Key West

Featured Vacation Homes in Monroe County

Outdoor pool, pool umbrellas, pool loungers
The Hammocks at Marathon

The Hammocks at Marathon

2.5 star property
Marathon
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
Pool
Tropical Key West out of the way

Tropical Key West out of the way

Stock Island
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
Exterior
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Marathon
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
Outdoor pool, a heated pool
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Old Town Key West
10.0 out of 10, Exceptional, (192)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is HK$7,388
HK$14,736 total
includes taxes & fees
16 Nov - 17 Nov
Perfect Location, Private Heated Pool, Pristine Luxury Home!
TV
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

Old Town Key West
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
Pool
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 star property
Rock Harbor
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
Exterior
Restful waterfront townhome with deck, great water views & washer/dryer

Restful waterfront townhome with deck, great water views & washer/dryer

Duck Key
9.2 out of 10, Wonderful, (89)
"Great place"
United States
Diego
Restful waterfront townhome with deck, great water views & washer/dryer
Fridge, microwave, oven, stovetop
Charming townhome with ocean views, an open porch & steps from the water

Charming townhome with ocean views, an open porch & steps from the water

Duck Key
9.4 out of 10, Exceptional, (9)
"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
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
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
Fridge, microwave, oven, stovetop
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Old Town Key West
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.
The price is HK$2,496
HK$5,190 total
includes taxes & fees
18 Nov - 19 Nov
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key
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.
The price is HK$2,333
HK$5,364 total
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water
Beach nearby, sun-loungers, beach towels
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Key Largo
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.
The price is HK$731
HK$2,324 total
includes taxes & fees
1 Dec - 2 Dec
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Marina
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Duck Key
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
Outdoor dining
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
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!
Outdoor dining
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

Old Town Key West
9.8 out of 10, Exceptional, (81)
"Incredible Stay! "
United States
Jill Z.
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Property grounds
Waterfront escape with stunning views, private balconies, near attractions

Waterfront escape with stunning views, private balconies, near attractions

Duck Key
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
Outdoor dining
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key
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
Living area
Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!

Old Town Key West
9.8 out of 10, Exceptional, (20)
"Awesome location with excellent communication. "
United States
Gary W.
The price is HK$1,112
HK$3,078 total
includes taxes & fees
16 Nov - 17 Nov
Kingfish Keep | Lively Escape on Duval! Balcony!
Outdoor pool, a heated pool
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8

PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8

Stock Island
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
Pool
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key
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

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Clain for one of the nicest places in Key West"
luis 1-night trip
Posted 14 hours ago
Beachside Resort & Residences

Find out more about Monroe County

Monroe County Vacation Homes information

Number of reviews
1,657
Accommodation
3860 Vacation Homes
Lowest Price
HK$2,324
Highest Price
HK$14,736