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Luxury Vacation Rentals in Key West with an Ironing Board

We may have luxury vacation rentals here in Key West, but we take our casual apparel very seriously. However, that's not to say that we don't have some fine restaurants and other attractions where you may want to bust out of your rental looking top notch. That's why all rentals come with an ironing board so your threads can be in prime condition for your hot night out at the Sunset Celebration or dancing the night away at one of the popular night life destinations.
Your search has found 87 homes
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Showing homes 1 - 25 of 87

CORAL HAMMOCK 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$150 -
$1,906

CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Open and airy, with private balconies, a grand 52" flat screen TV in the living room and well-equipped kitchen. A short walk to the community pool and a short drive to favorite local watering holes.



OLD TOWN 3 Bedroom Home Key West, FL 3 bedrooms
2 baths
$450 -
$5,655

BAHAMA DREAMING: A beautifully renovated Conch house conveniently located in the center of Old Town, one-half block behind Duval Street.  3 bedrooms and 2 baths with queen sleeper sofa offers a comfortable sanctuary for up to 8 people.  Private backyard for lounging by the pool and dining outdoors make this home an ideal choice to enjoy both the quiet and chaotic sides of Key West.



TRUMAN ANNEX 3 Bedroom Condo Key West, FL 3 bedrooms
2 baths
$2,000 -
$5,075

KEY WEST CASA: Beautiful and spacious Shipyard condominium, Key West Casa is one of only a few 3 bedroom 2 bath condos. Located in the prestigous Truman Annex community just 2 blocks to infamous Duval Street and walking distance to the beach, Sunset Celebration and anything you want to do on our island paradise.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$345 -
$3,369

KEY WEST CROWN JEWEL: We know that you will enjoy staying in our little bit of Paradise. This is a 2 bedroom, 2 bath Penthouse condominium with 1350 square feet of living space. Located on the Atlantic Ocean with magnificent views from every room. A short bike ride downtown and you are in the midst of what has made Duval Street infamous: bars, restaurants, and galleries galore.



OLD TOWN 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1 bath
 

EMMA'S SECRET (monthly rental):  Luxurious 2 bedroom 1 bath condominium located in the historic Bahama Village neighborhood of Old Town offers all the amenities of home.  Enjoy the tropical backyard ambience with jacuzzi, pool and tiki hut.   Located in walking distance to Duval Street, the heart of Key West with all the activities, restaurants, speciality shops and nightlife.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

VERANDAH (monthly rental): Tucked away on Frances Street lies your island escape called Verandah, named for the lanai surrounded by Bahama shutters allowing tropical breezes to waft through. A stunning 2 bedroom 2 bath home with private pool in a quiet residential neighborhood with plenty of space for your family to stay and play!



GOLF COURSE 2 Bed Condo - Monthly KEY WEST, FL 2 bedrooms
2.5 baths
 

SOUTHERN COMFORT (monthly rental): Best of both worlds! Stay in a beautiful 2 bedroom 2.5 bath Conch-style home in the peaceful, gated Key West Golf Club community -- stroll the lushly landscaped grounds, take a swim, play some golf. Head out to some of our favorite local restaurants and marinas just across the road or to downtown Key West, 5 minutes farther down the road.



GOLF COURSE 2 Bed Home - Monthly Key West, FL 2 bedrooms
3 baths
 

CASA FLORA (monthly rental): This lovely home overlooks the greens at the Key West Golf Club. On the first floor you will find the kitchen, dining area, living room, den with sleeper sofa and a full bath. Upstairs are 2 bedrooms with baths ensuite. Relax in the luxury of your own backyard with private pool or take a stroll through the lushly landscaped grounds of this gated community.  



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

ATLANTIC BLUES (monthly rental):   A stylish example of Conch architecture, this 1 bedroom 1 bath cottage has been totally renovated with hardwood floors, beautiful glass tiles, shining granite countertops, top notch kitchen appliances and décor that is playful and soothing. Add the luxury of your own dipping pool and you know you have found your home.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$2,200 -
$4,250

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in secluded Truman Annex. Lots of open spaces, perfect for entertainig or keeping it low-key and intimate. Easy walking distance to all Key West has to offer.



GOLF COURSE 3 Bed Home - Monthly Key West, FL 3 bedrooms
2.5 baths
 

ISLAND BREEZE (monthly rental): Located in the exclusive Sanctuary within the Key West Golf Club, this spacious home allows for lots of visitors with 3 bedrooms plus a den off the living room with a sleeper sofa. Enjoy the quiet solitude of this secure gated community. And when you\\'re ready for the chaotic activity of Duval Street, you are a quick 10-minute drive away.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2.5 baths
 

EDEN ON EATON: You can have the best of both worlds, right here and now. Live in a historic Conch cottage with subtle details of days gone by, located in the middle of the action on Eaton Street in Old Town Key West. A quick walk or bike ride to the historic seaport, bars, restaurants, shops. Relax on the private deck or sip a cocktail on the front porch watching the people pass by.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

CONCH ESCAPE (monthly rental): 2 bedroom 2 bath cottage in a quiet Old Town neighborhood, this property has a renovated kitchen and other recent updates making it comfortable and inviting. Enjoy a cocktail on the private deck in your own backyard, or stroll over the the pool shared by an intimate group of neighbors.



OLD TOWN Studio Condo Key West, FL 1 bedroom
1 bath
$120 -
$1,740

OSPREY: This quaint cottage is located in The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West, just 2 blocks from Duval Street. Compact and well-appointed, it is perfect for two people who want to relax, swim and walk around Duval Street, day after day.



TRUMAN ANNEX 3 Bedroom Home Key West, FL 3 bedrooms
4 baths
$4,000 -
$9,200

EASY LIVIN': The name says it all! This lovely private 3 bedroom home with pool is located in a secluded cul-de-sac in Truman Annex, a gated community located in historic Old Town Key West. Lounge by the pool in peace and tranquility or take a short walk to Duval Street where you will find the restaurants, bars, and shopping you have heard so much about.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
1.5 baths
$1,300 -
$2,864

LINGER LONGER: Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome in the President's Walk of Truman Annex, a gated community located within Old Town Key West. This property is conveniently situated poolside and just a short walk to the many restaurants, attractions and shopping that make Key West so special.



GOLF COURSE 2 Bed Condo - Monthly Key West, FL 2 bedrooms
1.5 baths
 

LAKEVIEW (monthly rental): Come to Key West where the sun always shines!! Stay in a beautiful 2 bedroom 1.5 bath bungalow in the gated Key West Golf Club community. Stroll the lushly landscaped grounds, relax in the pool, play a round of golf, and when you venture out, you will be close to it all - beaches, downtown and some of our favorite local restaurants.



OLD TOWN 1 Bed Home - Monthly Key West, FL 1 bedroom
1 bath
 

CASITA de CATHERINE (monthly rental): Come stay and play in this cozy cottage only steps away from Duval Street! Sunny days and tropical breezes are guaranteed; it’s the perfect place to relax, rejuvenate, and relish all the greatness you came to expect for your stay in Key West. 1 bedroom with loft, private deck with jacuzzi, all the comforts of home, and more.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
1 bath
 

SUNNY DAYS (monthly rental): Beautifully maintained while retaining its original style and structure, this quaint 2 bedroom 1 bath cottage has Dade County pine throughout the property adding a feel of old Key West. The furnishings are tasteful and comfortable, the neighbors in this intimate compound are friendly and the pool and jacuzzi are inviting.



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2.5 baths
$1,500 -
$2,900

A PLACE IN PARADISE:  You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-style townhome in prestigious Truman Annex. Spend your vacation in a quiet gated community surrounded by historic buildings and tropical flora that exemplifies the best of Key West. Walk two blocks to all that Duval Street has to offer.



OCEAN SIDE 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$225 -
$2,381

BRISA DEL MAR: This 2 bedroom, 2 bath condominium is located oceanfront in a gated community with a spectacular view of the Atlantic Ocean. Walk across the street to the beach and rent umbrellas, chairs, kayaks; enjoy a sno-cone after playing volleyball or just sit on your balcony and relax in the tropical breezes with a margarita.  Now, this is livin'...



TRUMAN ANNEX 2 Bedroom Condo Key West, FL 2 bedrooms
2 baths
$1,300 -
$2,791

CONCH CONDO: This 2 bedroom 2 bath second-floor condo features a fully-equipped kitchen, home theatre in the living room, plasma TVs in both bedrooms, soaring cathedral ceilings with ceiling fans and central air conditioning. Located in Truman Annex within walking distance of everything Key West has to offer; you have found a true Paradise.



OLD TOWN 2 Bed Home - Monthly Key West, FL 2 bedrooms
2 baths
 

KEY LIME PIE (monthly rental): A little slice of paradise located one block from the Historic Seaport on a tiny lane. Close enough to bike to all the sights and attractions of Old Town; far enough away to forget you are staying right in the middle of the action. 2 bedrooms 2 baths with private swim spa, this home will give you a reason to say, Ahhh...



TRUMAN ANNEX 2 Bedroom Home Key West, FL 2 bedrooms
2.5 baths
$1,700 -
$3,625

ARTIST GARDEN:  A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of Truman Annex, a gated community within Old Town Key West. This property is in the ideal location, in walking distance to all Old Town has to offer, including the beautiful beach at Fort Zachary Taylor State Park.



OCEAN SIDE 3 Bedroom Condo Key West, FL 3 bedrooms
2 baths
$375 -
$4,344

SURF SIDE - Search no further! This fabulous condominium is directly on the Atlantic Ocean. Located at the end of the building closest to the beach, the balcony wraps around offering full ocean views from the 3 bedrooms and the living room. Stylish furnishings, well-equipped kitchen and all the modern conveniences are here for your pleasure.



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Showing homes 1 - 25 of 87