Monthly Rentals


Properties Available 49 properties available
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d
Casa Oliviana
Private Home Pet Friendly
$395.00 - $1,254.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (33)
Like many highlights of Key West, THE ADMIRAL'S ESTATE celebrates a rich history of the island while embracing a modern restoration. THE ADMIRAL'S ESTATE is a true historic Key West home, originally built for a high-ranking Naval Officer in the early 1900s. This impressive estate is armed with two living areas, a top-of-the-line gourmet kitchen, cl
The Admiral's Estate
Private Home
$500.00 - $1,445.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (2)
THE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple that graces the front door – one of the many subtle touches that adds to the charm. THE GILDED PINEAPPLE features a
Hot HOT 30
The Gilded Pineapple
Private Home Pet Friendly
$400.00 - $1,200.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
SPIRIT OF KEY WEST was originally built in 1893 and features that authentic Key West charm found in other historic properties such as Hemingway’s House, Asa Tift’s manor and Truman’s Little White House. The vaulted ceilings and Dade County Pine walls harken back to a time when the cigar industry was booming and Key West featured more millionaires p
Hot HOT 41
Spirit of Key West
Private Home
$482.00 - $1,156.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (1)
Imagine your whole group staying in one home, with everyone having their own private bedroom suite. At CASA SUITE CASA, all four bedrooms are laid out as suites; each with an en-suite bathroom and flat screen TV. And that's just the beginning! A large private pool surrounded by tropical gardens, an expansive living area, and an ideal location close
Casa Suite Casa
Private Home
$300.00 - $1,000.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (19)
Get ready to reel in Last Key Realty’s newest vacation home! THE WICKED TUNA is a classic Key West home located in one of the most desirable areas of Old Town. This tastefully restored home features a historic appearance and charm, while offering all the modern conveniences one could desire. Located just down the street from the historic seaport, y
Hot HOT 45
The Wicked Tuna
Private Home Pet Friendly
$250.00 - $725.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
SUNDRENCHED REFLECTIONS is very close to Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large sundrenched balcony overlooking Florida Bay and the Gulf of Mexico beyond. THE PRIVATE GATED COMMUNITY... Sunset Marina is a gated community located on Stock Island, right off the entrance t
Sundrenched Reflections
Condo
$175.00 - $487.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
PERFECT HARMONY is a unique one-story home that features an ideal balance between modern touches and tropical styling. With its high ceilings, spacious kitchen, and outdoor lounge beside the pool; PERFECT HARMONY has everything you could desire in a vacation rental. Most importantly, this stylish home includes full-time guest services from Last Key
Perfect Harmony
Private Home Pet Friendly
$222.00 - $646.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)
In the Historic Seaport area of Old Town, there is a house that will behold your eye. At first glance you'll see that HEAVENLY ZEN is beautifully maintained with carefully tended landscaping; however, nothing will prepare you for what is inside. As you walk in, you will feel an immediate sense of peace and relaxation. All of the spaces in this meti
Hot HOT 30
Heavenly Zen
Private Home Pet Friendly
$375.00 - $1,271.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (44)
A home designed to impress the most discerning travelers, LAYOVER IN PARADISE is an oasis of comfort sure to meet the expectations of those accustomed to first class treatment. LAYOVER IN PARADISE is a newly constructed private home in the Casa Marina neighborhood that offers three spacious private suites, each with a large en-suite bathroom - and
Layover In Paradise
Private Home Pet Friendly
$333.00 - $895.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
MODERN IN THE MEADOWS proves you can blend modern and tropical styles into a beautifully laidback yet chic home. This fabulous monthly rental shines with its high-end upgrades, refined decor and upscale accommodations. Located in the quiet, sought-after Meadows neighborhood you’ll be treated to a month of relaxation in a newly renovated home that f
Modern in the Meadows
Private Home Pet Friendly
$295.00 - $1,015.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (5)
SWEPT AWAY is a meticulously renovated and decorated one-story private home with a refreshing mix of that classic conch home feel we all adore and a new coastal style. This conch cottage has an open living plan and a lovely backyard garden area with a private pool, ideal for relaxing in your oasis just blocks from the famous sites of Old Town Key W
Hot HOT 31
Swept Away
Private Home Pet Friendly
$210.00 - $590.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (21)

Tell us what you're looking for and someone will contact you with available options.

I agree