Key West 3 Bedroom Monthly Home & Condo Rentals
18 properties available
It is not so often that something new is built in Old Town, the historic district of Key West known for quintessential conch homes and walkable streets. But recently a spectacular development called Old Town Villas was constructed smack dab in the middle of Old Town. SEAPORT SENSATION is one of the newly built breathtaking townhomes at Old Town Vil
Seaport Sensation
Townhome
$275.00 - $877.00 / per night
3
bedrooms
3
baths
1
half-baths
8
guests
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
The Gilded Pineapple
Private Home
$400.00 - $1,200.00 / per night
3
bedrooms
3
baths
6
guests
CASA AVILA combines a rich history with a desirable Old Town location. Located two blocks from both the waterfront and Duval Street, this beautiful home is considered one of Old Town's original Grande Dames and proudly displays a historical preservation star. CASA AVILA was Key West's first prominent art gallery and one of the original homes in Old
Casa Avila
Private Home
$300.00 - $915.00 / per night
3
bedrooms
3
baths
8
guests
For a month in Key West it is ideal to harness the comforts of new construction similar to the luxuries of your own home, but keeping the true spirit of Old Town Key West and the magical surprises around every corner. This brand newly constructed home, located a stone's throw from the Southernmost Point, also backs up to the famous Butterfly Museum
Dance of the Butterflies
Private Home
$250.00 - $766.00 / per night
3
bedrooms
3
baths
8
guests
5
(6)
Imagine a traditional conch home in the Solares Hill section of Old Town. MAISON TROPICALE is stunningly restored then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with unique show pieces. This brilliant decor is set against a backdrop of original Dade Cou
Maison Tropicale
Private Home
$250.00 - $825.00 / per night
3
bedrooms
3
baths
8
guests
5
(18)
Upscale island living is epitomized with this beautiful home, CAYO CALYPSO. This modern home is well appointed, spacious and comfortable. CAYO CALYPSO offers a relaxing tropical theme and prime location near the Beach. Enjoy easy walks to Higgs Beach and pier, community playgrounds, Salute Ristorante or Smathers Beach. Comfortable accommodations in
Cayo Calypso
Private Home
$215.00 - $875.00 / per night
3
bedrooms
3
baths
8
guests
5
(26)
MODERN MAJESTY is a stunning, freshly renovated three-bedroom condo that checks every box for the perfect vacation rental. This large unit is laid out over one floor, meaning you don’t have to worry about stairs. The three bedrooms are luxuriously appointed suites, each with their own en-suite bathroom. The kitchen is as functional as it is beautif
Modern Majesty
Condo
$325.00 - $1,070.00 / per night
3
bedrooms
3
baths
1
half-baths
6
guests
5
(2)
SUNSET POINT has everything you could want in a vacation home: it is close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET POINT with a very large balcony overlooking the Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated communit
Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Sunset Point
Condo
$175.00 - $495.00 / per night
3
bedrooms
2
baths
6
guests
5
(23)
SUNSET DREAMS has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET DREAMS with a large balcony overlooking Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated community
Sunset Dreams
Condo
$175.00 - $495.00 / per night
3
bedrooms
2
baths
8
guests
5
(12)
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
$222.00 - $655.00 / per night
3
bedrooms
3
baths
6
guests
5
(3)
From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage
Carefree on Cudjoe
Private Home
$265.00 - $924.00 / per night
3
bedrooms
3
baths
9
guests
5
(3)
ISLAND BLISS is a classic Old Town Key West home, complete with delicate gingerbread accents, a classic Southern front porch with rocking chairs, and lush, tropical foliage tastefully surrounding the property. This beautiful, historic two-story home has been lovingly cared for and restored with a mix of modern touches and traditional Key West influ
Island Bliss
Private Home
$250.00 - $720.00 / per night
3
bedrooms
2
baths
8
guests
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