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

Monroe County Vacation Rentals

Browse 14,742 available vacation homes and compared across 31 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 Key West
House with terrace, private pool & yard | Close to Duval Street | City view
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House Marathon
Vacation home with terrace, BBQ & private pool
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House Big Pine Key
Christmas in the FL Keys! Stunning sunsets, beaches 10 min away, Fishing!
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House Key West
Casa de Rosalie by AvantStay | Great Location w/ Pool, BBQ & Outdoor Dining | Month Long Stays Only
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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 | Nature view
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Villa Marathon
Beachfront 8-bedroom villa
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House Key West
Fully equipped charming house with BBQ, jacuzzi & terrace | Perfect for remote work | Pets allowed
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House Little Torch Key
Vacation home with private pool & BBQ
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House Marathon
Vacation home with heated pool, barbeque & terrace
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House Marathon
Vacation home with patio, barbecue & pool | Nature view
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House Marathon
Fully equipped house with jacuzzi, grill & private pool | Suitable for remote work
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House Islamorada
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
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House Marathon
2 Incredible Waterfront Homes - One Low Price!
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House Marathon
Vacation home with barbeque, private pool & patio
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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 14,742 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Layton
House ∙ 8 guests ∙ 2 bedrooms

House with pool, grill & hot tub | Nature view

Layton, Monroe County, Florida, United States
This house rental in Layton accommodates 8 guests and features a relaxing hot tub for your enjoyment.
from $88
per night
(16)
View deal
House Key Largo
House ∙ 5 guests ∙ 2 bedrooms

Child-friendly pleasant house with barbecue

Key Largo, Monroe County, Florida, United States
This house rental in Key Largo accommodates 5 guests and features family-friendly amenities for a comfortable stay.
from $130
per night
(5)
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House Key West
House ∙ 4 guests ∙ 2 bedrooms

House with yard, terrace & pool | Sea view

Key West, Monroe County, Florida, United States
Charming house rental in Key West for 4 with a pool and easy beach access, perfect for a relaxing getaway.
from $242
per night
(1)
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House Islamorada
House ∙ 14 guests ∙ 6 bedrooms

Family-oriented beautiful vacation home with barbecue, private pool & yard

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 14 guests and features a private pool for relaxation and fun.
from $688
per night
(1)
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House Marathon
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped house with patio, private pool & barbecue | Nature view | Pets are welcome

Marathon, Monroe County, Florida, United States
This house rental in Marathon accommodates 10 guests and features a private pool for a relaxing getaway.
from $484
per night
(13)
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House Cudjoe Key
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with terrace, grill & hot tub | Nature view

Cudjoe Key, Monroe County, Florida, United States
This house rental in Cudjoe Key accommodates 10 guests and features a private pool for a relaxing getaway.
from $665
per night
(128)
View deal
House Marathon
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped vacation home with grill & heated pool | Nature view

Marathon, Monroe County, Florida, United States
This house rental in Marathon accommodates 8 guests and features a private pool for relaxation.
from $378
per night
(12)
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House Key West
House ∙ 12 guests ∙ 6 bedrooms

House with yard, BBQ & private pool | Next to West Martello Tower

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 12 guests and features a private pool for a relaxing getaway.
from $318
per night
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House Key Largo
House ∙ 9 guests ∙ 4 bedrooms

Family-oriented spacious vacation home with sauna, patio & garden | Perfect for remote work | Pets are welcome

Key Largo, Monroe County, Florida, United States
This house rental in Key Largo accommodates 9 guests and features a family-friendly kitchen perfect for gatherings.
from $201
per night
(4)
View deal

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