Monroe County Vacation Rentals - HolidayHomes base64Hash Monroe County Vacation Rentals - HolidayHomes

Monroe County Vacation Rentals

Browse 14,680 available vacation homes and compared across 35 trusted partners

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Top-Rated Vacation rentals in Monroe County

Book the highest-rated Monroe County vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Marathon
Children-friendly house with heated pool, barbeque & terrace | Pets allowed
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House Key Largo
Vacation home with yard, patio & heated pool
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House Marathon
Vacation home with garden, barbecue & private pool
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House Islamorada
Blue Dolphin Oceanfront Estate, Millionaire's Row, Private Saltwater Pool
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House Marathon
House with patio, private pool & barbecue | Nature view
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House Sugarloaf Shores
Vacation home with barbeque, private pool & terrace
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House Key Colony Beach
Vacation home with terrace, pool & grill | Nature view
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House Marathon
UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH!
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House Marathon
Fully equipped spacious house with terrace & barbecue | Close to the beach
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House Marathon
Immediate Availability, Beach, 70 ft Dock - Marathon VACA-23-16 Entire House
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House Key West
Vacation home with hot tub, private pool & patio | Next to West Martello Tower | City view
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House Key Largo
ESCAPE TO PARADISE! WATERFRONT PROPERTY! LOWEST PRICE IN THE KEYS! BEST LOCATION
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House Islamorada
House with private pool
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House Islamorada
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
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House Key West
Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
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Top 15 most Recommended Vacation Rentals in Monroe County

Discover your ideal Monroe County vacation rental with real-time comparisons of 14,680 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Key West
House ∙ 10 guests ∙ 3 bedrooms

155 m² House

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 10 guests and features a private pool for a relaxing stay.
from $236
per night
(18)
View deal
House Big Pine Key
House ∙ 12 guests ∙ 5 bedrooms

223 m² House

Big Pine Key, Monroe County, Florida, United States
Spacious house rental in Big Pine Key accommodates 12 guests and features a private pool for a relaxing getaway.
from $591
per night
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House Big Pine Key
House ∙ 8 guests ∙ 3 bedrooms

112 m² House

Big Pine Key, Monroe County, Florida, United States
This house rental in Big Pine Key accommodates 8 guests and features a waterfront view for a relaxing stay.
from $237
per night
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House Marathon
6 guests ∙ 3 bedrooms

House

Marathon, Monroe County, Florida, United States
This house rental in Marathon accommodates 6 guests and features a family-friendly kitchen and a private pool for relaxation.
from $302
per night
(13)
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Cabin Big Pine Key
4 guests ∙ 1 bedroom

Cabin

Big Pine Key, Monroe County, Florida, United States
Charming cabin in Big Pine Key accommodates 4 guests and features convenient beach access for a relaxing getaway.
from $165
per night
(189)
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House Marathon
10 guests ∙ 4 bedrooms

House

Marathon, Monroe County, Florida, United States
Spacious house rental in Marathon accommodates 10 guests and features a refreshing pool for relaxation.
from $454
per night
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House Marathon
10 guests ∙ 4 bedrooms

House

Marathon, Monroe County, Florida, United States
This house rental in Marathon accommodates 10 guests and features a private pool for a relaxing getaway.
from $444
per night
(10)
View deal
House Key West
House ∙ 6 guests ∙ 2 bedrooms

88 m² House

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 6 guests and features a kitchen for your convenience.
from $215
per night
(94)
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House Key Colony Beach
House ∙ 10 guests ∙ 3 bedrooms

193 m² House

Key Colony Beach, Monroe County, Florida, United States
This spacious house rental in Key Colony Beach accommodates 10 guests and features a beautiful waterfront view.
from $239
per night
(8)
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