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

Monroe County Vacation Rentals

Browse 15,012 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 Islamorada
Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
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House Marathon
Vacation home with patio, barbecue & pool
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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 Colony Beach
Vacation home with hot tub, patio & pool
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House Marathon
World class ocean views on a sugar sand beach!
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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
House with patio, barbecue & private pool | Perfect for remote work
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House Cudjoe Key
PARADISE 3 MINUTES TO OPEN WATER-60FT DOCK-WIDE CANALRESERVE AREA-CUDJOE KEY
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House Key West
Welcome To Poseidon's Paradise Midtown Home & Incredible Pool 28 Nights Min
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House Marathon
Oceanfront Family Retreat - Stunning Views Lindsay Landing! Beach/Pool Access!
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House Marathon
House with pool, BBQ & terrace
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House Key Largo
House with barbeque & terrace
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Cabin Key West
Cottage with private pool & BBQ | Near West Martello Tower | City view
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House Islamorada
House with terrace, heated pool & barbeque
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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 15,012 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Cudjoe Key
House ∙ 6 guests ∙ 2 bedrooms

89 m² House

Cudjoe Key, Monroe County, Florida, United States
This house rental in Cudjoe Key accommodates 6 guests and features a family-friendly yard perfect for outdoor activities.
from $160
per night
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House Bahama Village
House ∙ 4 guests ∙ 2 bedrooms

65 m² House

Bahama Village, Key West, Monroe County
Charming house rental in Bahama Village, accommodating 4 guests, featuring beach access for a perfect getaway.
from $186
per night
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House Big Pine Key
House ∙ 6 guests ∙ 3 bedrooms

111 m² House

Big Pine Key, Monroe County, Florida, United States
This house rental in Big Pine Key accommodates 6 guests and features a family-friendly yard for outdoor enjoyment.
from $199
per night
(10)
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House Islamorada
8 guests ∙ 4 bedrooms

House

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a spacious balcony for relaxing and enjoying the views.
from $630
per night
(14)
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House Key West
16 guests ∙ 6 bedrooms

House

Key West, Monroe County, Florida, United States
This spacious house rental in Key West accommodates 16 guests and features a private pool for ultimate relaxation.
from $946
per night
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House Big Pine Key
House ∙ 7 guests ∙ 3 bedrooms

126 m² House

Big Pine Key, Monroe County, Florida, United States
This house rental in Big Pine Key accommodates 7 guests and features a private pool for a relaxing getaway.
from $183
per night
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House Key Largo
6 guests ∙ 3 bedrooms

House

Key Largo, Monroe County, Florida, United States
This house rental in Key Largo accommodates 6 guests and features a spacious yard perfect for outdoor activities.
from $117
per night
(20)
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House Key Colony Beach
House ∙ 6 guests ∙ 3 bedrooms

136 m² House

Key Colony Beach, Monroe County, Florida, United States
This house rental in Key Colony Beach accommodates 6 guests and features a waterfront view.
from $213
per night
(12)
View deal
Cabin Monroe County
Cabin ∙ 8 guests ∙ 2 bedrooms

98 m² Cabin

Monroe County, Florida, United States
This charming cabin in Monroe County accommodates 8 guests and features a spacious yard perfect for family gatherings.
from $160
per night
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