Florida Keys Vacation Rentals - HolidayHomes base64Hash Florida Keys Vacation Rentals - HolidayHomes

Florida Keys Vacation Rentals

Browse 14,632 available vacation homes and compared across 29 trusted partners

Anytime
Guests
Anytime
Guests

Top-Rated Vacation rentals in the Florida Keys

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

House Cudjoe Key
Fully equipped vacation home with terrace, grill & private pool | Good for workation | Pets allowed
Book now
House Big Pine Key
Christmas in the FL Keys! Stunning sunsets, beaches 10 min away, Fishing!
Book now
Accommodation Key West
Rental with pool, yard & terrace | Next to Duval Street
Book now
House Marathon
Classic Waterfront estate in beautiful Sombrero Beach - over 200' of dock space
Book now
House Marathon
Children-friendly house with heated pool, barbeque & terrace | Pets allowed
Book now
Villa Marathon
Beachfront 8-bedroom villa
Book now
House Key Largo
Vacation home with yard, patio & heated pool
Book now
House Key West
Fully equipped charming house with BBQ, jacuzzi & terrace | Nature view | Perfect for remote work | Pets allowed
Book now
House Marathon
Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch
Book now
House Islamorada
Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
Book now
House Marathon
Vacation home with patio, barbecue & pool
Book now
House Marathon
2 Incredible Waterfront Homes - One Low Price!
Book now
House Marathon
Vacation home with barbeque, private pool & patio
Book now
House Stock Island
Fully equipped charming vacation home with barbecue, patio & garden
Book now
House Key West
Vacation home with hot tub, private pool & patio | Next to West Martello Tower | City view
Book now

Top 15 most Recommended Vacation Rentals in the Florida Keys

Discover your ideal Florida Keys vacation rental with real-time comparisons of 14,632 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Stock Island
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped lovely house with grill, pool & patio | Close to Key West Tropical Forest & Botanical Garden | Pool view

Stock Island, Monroe County, Florida, United States
This house rental in Stock Island accommodates 4 guests and features a refreshing pool for relaxation and enjoyment.
from $124
per night
(3)
View deal
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 $516
per night
View deal
House Marathon
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with patio, private pool & grill

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 $338
per night
(16)
View deal
House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, barbeque & heated pool | Perfect for remote work

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 8 guests and features a heated pool for a relaxing stay.
from $536
per night
(59)
View deal
House Marathon
House ∙ 8 guests ∙ 3 bedrooms

House with patio, private pool & barbecue

Marathon, Monroe County, Florida, United States
This house rental in Marathon accommodates 8 guests and features a private pool for a relaxing getaway.
from $379
per night
(71)
View deal
House Islamorada
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with private pool, BBQ & jacuzzi | Suitable for remote work

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 10 guests and features a private pool for a relaxing getaway.
from $507
per night
(4)
View deal
House Marathon
House ∙ 14 guests ∙ 6 bedrooms

Child-friendly lovely house with pool, barbeque & hot tub | Dogs allowed

Marathon, Monroe County, Florida, United States
Spacious house rental in Marathon for 14 guests featuring a family-friendly kitchen and a relaxing pool.
from $891
per night
(51)
View deal
House Key Colony Beach
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with terrace, heated pool & barbeque | Nature view | Pets allowed

Key Colony Beach, Monroe County, Florida, United States
This house rental in Key Colony Beach accommodates 6 guests and features a heated pool for your enjoyment.
from $197
per night
(15)
View deal
House Islamorada
House ∙ 4 guests ∙ 2 bedrooms

House with yard, patio & barbeque | Nature view

Islamorada, Monroe County, Florida, United States
This house rental in Islamorada accommodates 4 guests and features a waterfront view with a spacious yard.
from $242
per night
(14)
View deal

More travel options

image-tag