Key West Holiday Rentals

Key West Holiday Rentals By Owner & Vacation Homes

More Cities

About Key West


Holiday Rentals

Welcome to Hyatt Vacation Club at Windward Pointe Whether you choose to spend your days simply relaxing by the infinity pool or setting off on a div


Beds: 2 Baths: 2 Sleep: 6

Beds: 2 Baths: 2 Sleep: 6

Welcome to Hyatt Residence Club Key West, Sunset Harbor Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perf


Beds: 1 Baths: 1 Sleep: 4

Beds: 1 Baths: 1 Sleep: 4

Located in one of Key West's most striking gated waterfront luxury neighborhoods, 'Foundry on the Waterfront' provides a unique opportunity


Beds: 3 Baths: 3 Sleep: 10

Beds: 3 Baths: 3 Sleep: 10

The home is nothing short of pure perfection. A completely turnkey, fully accommodating monthly vacation rental in Key West is very hard to come by, but


Beds: 4 Baths: 3 Sleep: 12

Beds: 4 Baths: 3 Sleep: 12

Offering amazing views of the ocean, our Key West condo near beach is a perfect base to enjoy your sun and sand holiday. This beautifully furnished 2 be


Beds: 2 Baths: 2 Sleep: 6

Beds: 2 Baths: 2 Sleep: 6

Accommodations: 2 bedrooms, 2 full bathrooms, pull out bed int the living room (sleeps up to 6). This 2 BR Key West, Florida vacation r


Beds: 2 Baths: 2 Sleep: 6

Beds: 2 Baths: 2 Sleep: 6

Beach Bungalow - Key West Vacation Rentals. This warm and intimate new 2 story vacation paradise was designed by a local Princeton trained architect,


Beds: 1 Baths: 1 Sleep: 4

Beds: 1 Baths: 1 Sleep: 4

Blending the outstanding amenities of one of the Florida\'s most celebrated oceanfront resorts with the charm of tropical residences, this exclusiv


Beds: 2 Baths: 1 Sleep: 3

Beds: 2 Baths: 1 Sleep: 3

Well maintained recently renovated luxury home with heated pool in very private yard. This charming home was built in 1918 so it has historical charm wi


Beds: 0 Baths: 3 Sleep: 10

Beds: 0 Baths: 3 Sleep: 10

Casa Diamante is a beautiful three bedroom, two and a half bathroom home in the perfect location of downtown Key West. This newly renovated home is sure


Beds: 0 Baths: 2 Sleep: 6

Beds: 0 Baths: 2 Sleep: 6


About Holiday Rentals

Explore your favorite property type: 
Caribbean vacation home rentals is here to provide you a large number of properties, each one with a unique style including Vintage and Trendy vacation rentals such as cabin, castle, condo, cottage, duplex, chalet, estate, farmhouse etc.
 
Find the best location to stay in Caribbean:
Here, you are going to get your stay near most adorable locations in Caribbean:-
A. Jamaica, which is also known as “The land of wood and water”.
B. Puerto Rico
C. Punta Cana, Dominican Republic
D. Aruba
E. Barbados
F. Grand Cayman, Cayman
 
These are the top rated destinations where one loves to stay. Caribbean vacation homes rental are also providing you the most adorable homes at breathtaking locations such as beachfront, oceanfront, city centre, lake view etc.
 
Find the best accommodations around Caribbean:
We are offering the best accommodations around Caribbean with the facility of booking at
- No booking fee
- No service fee
 
We have around 12000 properties which are perfect for business and touristic travelers, And also suitable for single, couple, group of friends and great for families. Book your favorite property to stay at beautiful, spacious, and comfortable vacation rentals at affordable prices.
 
Most popular tourist attractions to visit in Caribbean:
Caribbean is a lovely region and one can explore it fully to get the best experience of life. The most popular tourist attractions to visit are:-
A. Varadero, Punta Cana, Aruba, Barbados, Negril etc for beach lovers.
B. Montego, Cabarete, Grant Cayman, Cayman Island for adventure seekers.
C. Puerto Plata, Dominican Republic, Ocho rios, Saint kitts, San Juan are great to explore with families.
 
Convenient home rentals for air travelers in Caribbean
Caribbean vacation home rentals are providing a large number of home rentals near airport. The airports with a large no. of home rentals in Caribbean are:-
A. Luis Munoz Marin International Airport, San Juan, Puerto Rico
B. Punta Cana International Airport, Punta Cana, Dominican Republic
C. Jose Marti International Airport , Havana, Cuba
D. Queen Beatrix International Airport, Aruba
E. Las Americans International Airport, Santo Domingo
F. Lynden Pindling International Airport, Nassau, Bahamas
And for other airports in Caribbean, you can use our search bar to access the selection of vacation rentals available.  
 
Best time to visit - The Caribbean and its climate
The Caribbean is a beautiful region that consist of the Caribbean Sea, its island and the surrounding coasts, so that its weather. And it is famed for having the most desirable climate on the planet; it’s never too cold, never sweltering and rainfalls to a nice predictable rhythm.
The best time to visit The Caribbean is
1. December to April, the peak months  (drier, cooler, less humid)
2. September to October – the most prolific for hurricanes.