Take a Long Vacation to Key West

Rent Key West Vacations manages an amazing variety of Key West Monthly Rentals. Our townhomes, condos, and cottages are located in Old Town on Duval Square, near Key West’s famous attractions and nightlife. Many of our monthly rentals feature private pools and classic Key West architecture.

Key West is the perfect place to relax, escape, and enjoy the Florida beach life. Upon arriving in Key West, you’ll immediately feel its energy. The longer you stay, the more you can enjoy it.

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Living the Dream

Living the Dream

3 3 6 Key West
From $293.00/night
My Southernmost Kentucky Home

My Southernmost Kentucky Home

3 3 6 Key West
From $284.00/night
Ole' Olivia

Ole' Olivia

4 3.5 6 Key West
From $276.00/night
Olivia's Landing

Olivia's Landing

1 1 2 Key West
From $103.00/night
Olivia's Nest

Olivia's Nest

1 1 4 Key West
From $101.00/night
Olivia’s Retreat

Olivia’s Retreat

2 2 4 Key West
From $154.00/night
Pineapple Cottage

Pineapple Cottage

2 3 4 Key West
From $132.00/night
Portside Suite @ Tucked Away

Portside Suite @ Tucked Away

1 1 3 Key West
From $95.00/night
Reynolds Retreat

Reynolds Retreat

3 3 6 Key West
From $232.00/night
Royal Haven

Royal Haven

3 2 6 Key West
From $234.00/night
Sans Souci

Sans Souci

3 3 7 Key West
From $197.00/night
Soleil Chalet

Soleil Chalet

3 3 8 Key West
From $262.00/night