Preferred Properties

"Preferred for a Reason!"
Vacation Rentals in Key West
1.Location, Location

2.Luxurious Amenities

3.Professional Service

4.Convenience

5.Seriously Clean
Why stay at a pricey hotel with small rooms when you can rent one of our beautiful and spacious Key West condos or homes. These aren’t just your average vacation rentals; they are completely furnished with full kitchens, dining areas, patios, and more! Choose from a variety of floor plans and amenities that will allow you to experience the true island lifestyle, and make your vacation a memorable one.

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  1. Baya House/606 Truman Ave # 13

    The Baya House is a lovely Conch Style Key West Vacation home! Covered porches and balconies overlooking Windward Park, tucked away in a corner. This unit has tropical spirit, bringing the outside inside. The interior is attractively decorated with fun island décor! This is truly a comfortable vacation destination for all ages. The first floor is open-concept allowing a flow into each section of the home. The brand new, well equipped kitchen is perfect for cooking and entertaining. The dining area and living room are under grand cathedral ceilings that create grandeur in the tropics of Key West. The first floor bedroom has 2 twin beds (can be converted to a king), and a full en-suite bath. The room also has French doors opening to a private deck with seating and/or dining areas. The views from the balcony overlooks the pool and courtyard. A spacious master suite offers a queen bed and walk in closet. Just one block from Duval Street off of Truman Avenue, the Baya House is one of 13 units in Windward Park; a small and secure gated complex built around the courtyard featuring a 50’ x 20’ foot pool and lush, tropical landscaping. It is quiet and private while still being located right in the heart of Old Town. There is a parking space included as well as Wifi. Please note that all rules and regulations of Windward Park must be followed. This is a quiet residential complex. Estimated Square footage for this home is 1656 SQFT. (7 night stay required) There are also GREAT MONTHLY RATES! Access to pool (heated in the winter) Private rear deck Porch & Balcony Central A/C Telephone Cable TV DVD Player CD player Fully equipped Brand New Kitchen in 2013 Washer/Dryer Wireless Internet Parking for 1 car Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 2 beds, 2 bathrooms
    • View Details
    Baya House/606 Truman Ave # 13
    Key West FL
    24.552084, -81.797122
  2. BELLA VITA/ 410 Catherine St

    Southern Charm Looking to stay in Key West for a month or more? Want to be close to Duval St, but don’t want to hear the all the bar and street noise? Half a block from Southern Duval Street sits a charming, completely restored, historic home: offers every modern amenity such as a gourmet kitchen, modern baths, a wide covered porch overlooking the pool, and electronic gated parking. Three bedroom, two and a half bath home is within walking distance of all the restaurants, many local art galleries, and more attractions of Key West. If you have weekend company or just want extra space to park your bikes, or electric car, Southern Charm has plenty of parking and the gate is electronic. A covered porch overlooking the pool also has an entrance to the house. Step into the beautiful kitchen which features include stainlesss steel appliances, granite countertops, well stocked and equipped kitchen. The covered porch would make a nice setting for a romantic dinner or just a quiet evening around the pool. One of the guest bedrooms has access to the front porch. This room would be great for guests that like to keep late hours and don’t want to disturb others. Or maybe your an early riser and want to sit on the front porch as Key West wakes up. FEATURES: Cathedral Ceilings, Dade County Pine, Granite Countertops, Jacuzzi Tub, Steam Shower, Marble, Stained Glass Window, Electric Security Gate, Off Street Parking, Morro Fruit Tree, Pool Cabana, Outdoor Sound System, Bahama Shutters, Coral Rock Surrounding Pool. Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 3 beds, 2 bathrooms
    • View Details
    BELLA VITA/ 410 Catherine St
    410 Catherine St
    Key West FL
    24.548676, -81.798421
  3. Calico Cove/ 620 Thomas St #283

    (7 night stay required) - Calico Cove is a nicely appointed upstairs Vacation Condo in Key West with 2 balconies. Bright and clean end unit located in Shipyard of Truman Annex. Spacious living area with an open floor plan and glass doors that open to the rear balcony where you can sit back and relax. Well equipped kitchen with access to the front balcony. Master bedroom is decorated with new furniture, featuring a large queen bed, and second bedroom offers 2 twin beds with a flat screen TV. The bathroom has a shower with a bathtub and is centered between the two bedrooms. Calico Cove is just steps from the Shipyard pool where you can sit in a lounge chair and soak up some sun. (7 night stay required) Well equipped kitchen, bright and clean condo on the second level with front and rear porches. Flat screen Tv’s, CD player, DVD player, access to shared pool and off street parking for 1 car. Central AC and Washer/Dryer. Read more »
    • Key West, FL
    • Truman Annex
    • vacation rental
    • 2 beds, 1 bathrooms
    • View Details
    Calico Cove/ 620 Thomas St #283
    Key West FL
    24.553924, 81.799548
  4. Elizabeth's Secret/910 Elizabeth St. Private rear

    A tranquil and secluded flourishing tropical oasis awaits you behind the private gated entrance at Elizabeth’s Secret. A significant lot creates plenty of outdoor seating and a private pool (can be heated for an extra cost, please inquire before asking to have it heated). The shady side yard has room to relax while you grill, a covered front porch featuring a porch swing and sitting areas that are perfect when you want to get out of the sun but still able to visit with family and friends who can still lounge poolside. Inside this charming 2 bedroom 2 bath cottage, a bright and well equipped kitchen hosts a breakfast bar, open floor plan, cathedral ceilings, and a living area that has plenty of room to relax. Bring the outdoors inside by opening the French doors off the living room to the side deck where there is a space for outdoor dining. The master suite is decorated in bright colors, and has access to a private outdoor shower, (there is also a shower inside). The second bedroom is located in a large loft with a king bed. Amenities: Private Sunny Pool (can be heated but extra cost – inquire about cost) Gated Entry Full Equipped Kitchen Cable TV CD Player Wireless Internet DVD Player Washer/Dryer Telephone Central AC Off street parking for 1 car Charcoal Grill Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 2 beds, 2 bathrooms
    • View Details
    Elizabeth's Secret/910 Elizabeth St. Private rear
    Key West FL
    24.55305, -81.797493
  5. FLAGLERS FINEST: 1019 Flagler Ave

    Casa Marina House is a luxury vacation rental that you will fall in love with. Located in the exclusive Casa Marina, discover a home that has been transformed, preserving its historic fabric graciously blended with the very latest architectural design. Greeting you are awe inspiring 12 foot coffered ceilings with oversized moldings. French doors from every room reveal the lushly landscaped pool and loggia area for year round enjoyment. On the first level is a top of the line chef’s kitchen off the dining /living area, a large family room, a powder room and an en suite bedroom. Upstairs are 3 sumptuous bedroom suites and a large deck overlooking the beautiful pool and gardens. A pool house with full bath adds the perfect touch. Hurricane windows and doors. Circular driveway with covered off street parking. Read more »
    • Key West, FL
    • Casa Marina
    • vacation rental
    • 5 beds, 5 bathrooms
    • View Details
    FLAGLERS FINEST: 1019 Flagler Ave
    Key West FL
    24.549845, -81.788577
  6. Casa Royal/1219 Royal St

    Casa Royal, relax in superb luxury. This Key West Vacation home in Casa Marina has all the benefits a private community offers plus quality finishing’s. If you’re interested in spending a month or more in Key West, you will want to live here. Renovated with no expense spared, this modern build allows for serenity, entertainment and function. Past the gates, through the columns and large wooden doors are grand ceilings 18’ tall hosting tropically modern fans and high-tech lighting. The bamboo floors meet the dark, wooden furniture and cabinetry seamlessly. This open-concept home allows for a view of the main space as well as a direct view through the large French doors of the outdoor amenities. Casa Royal has two bedrooms and two bathrooms in the main house and two bedrooms and one bathroom in the guest house, a pool, outdoor shower, and cabana space with perfect sun lounging. The superbly designed kitchen plays the role as the epicenter of this living space. Granite counter top, breakfast bar, and every kitchen-aid under the tropical sun is here for your use. The compactor trashcan, wine fridge, large gas stove, and central AC controls make this home a fabulous place for entertainment and relaxation. The kitchen flows into the living and dining area. A large, wooden table seating four and an exceptional living room brings modern comforts alive. A large, cable flat screen television, WIFI, and a stockpile of games for all ages will surely delight! The open floor plan allows for keeping an eye on the children outside, but also allows for the division of spaces with blinds and closed doors to create intimate spaces and privacy. The master suite’s French doors open to the outdoor pool area. The high ceilings continue into the master, accentuated by a sky light and modern fan. There is a lounging space in the far end of the room for enjoying the cable television or for just relaxing. The master bath features a huge granite rain shower, and a modern, vessel sink. The master walk-in closet allows plenty of hanging and storage space. It also houses all extra linens. The second bedroom in the main house has a full size bed, plenty of windows for the tropical sun and closet space. There is also a full ensuite bathroom with two doors making it accessible from the living space. The main house also has a laundry room with a full washer/dryer, and cleaning supplies. The guest house consists of two bedrooms, one bathroom, and an outdoor shower. The first bedroom has a pull out couch, perfect for entertaining during the day and relaxing at night. The cable television and mini refrigerator make it easy to lounge and open up the French doors to bring the outside in. The second bedroom has a day bed, equipped with a trundle turning it into a queen. There is also a cable television and French doors in this room. The shared bathroom allows for privacy and ample use of the outdoor shower. Casa Royal makes the tropical outdoors accessible from all rooms. Key West is a place to take advantage of all the amenities: a heated pool, cabana, lounge chairs and guest quarters. Although there is a parking space behind gates, the prime location makes for an easy walk to almost any place in Key West. This is a luxurious yet casual and comfortable home. It is sure to make your vacation special. Amenities: Private residence featuring a sunny private heated pool, cabana, and lounging areas. Gourmet chef kitchen that is fully equipped including stainless steel appliances and prep sink, full laundry room with washer/dryer in the main house, WIFI, cable televisions, board games, cards etc., grill, off street parking, security system, central AC in main house, and window unit in guest house. Read more »
    • Key West, FL
    • Casa Marina
    • vacation rental
    • 4 beds, 3 bathrooms
    • View Details
    Casa Royal/1219 Royal St
    Key West FL
    24.551265, -81.793082
  7. Conch Cottage/ 722 Simonton St

    In the 20th century many residents of Key West began referring to themselves as “Conchs”, now this term generally applied to all residents of Key West. This vacation home is called Conch Cottage because it encompasses the heart of the Key West life style. In the heart of Old Town with traditional architecture, this home serves as a perfect luxury and vacation. Proximity to all that the island has to offer, Conch Cottage is a one bedroom, one bath home with a full kitchen and back deck. This rental is ideal for a couple or single guest. This home is exactly what you would imagine! From the ginger bread features to the porch seating area and colorful paint, this is a perfect place to people watch and relax at any hour of the day. Conch Cottage is fully furnished and features a completely renovated, fully equipped kitchen with stainless steel appliances. The living and dining areas are open concept. There is a flat screen, cable TV and couch. The open space allows full view of the French doors leading to your private rear deck. The bedroom has a queen bed and a door to the private back deck. You can close the curtains for privacy or let the sunshine come through. The rear deck has all the amenities you could need. The space has a lounging area, an outdoor seating area with an umbrella and a grill. This can serve as an outdoor dining area. The new spa is another way that this deck is the ultimate place to relax, entertain, grill and live like a local! Another bonus is the private, outdoor shower. You can slip away, allowing the tropical breeze in with no worries, there is complete privacy. If you want to take a swim, Key West has a community center with a huge community swimming pool and a deck overlooking the Atlantic Ocean. There is also a park next door to the pool, you may also want to take a bike ride in the Truman Annex, or ride to the tree-lined beaches of historic Ft. Zachary Taylor. Conch Cottage is a non-smoking home. Amenities Fully equipped kitchen Wireless Internet Cable TV DVD player Washer/Dryer – BOSCH stack-able Flat screen TV Split AC – bedroom and living room Outside dining/sitting area Charcoal Grill 2014 New Hot Tub Outside Shower (there is a shower inside as well) Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 1 beds, 1 bathrooms
    • View Details
    Conch Cottage/ 722 Simonton St
    Key West FL
    24.553924, -81.799548
  8. Corazon/601 Angela Street

    Private Heated Pool, Fully Equipped Kitchen, Stereo, CD player, DSL (Internet service), Cable TV, DVD, Washer/Dryer, Central A/C, and Private Parking. This home is a bright and colorful spacious 2 bedroom 2 1/2 bath located in the heart of Old Town. Open floor plan,fully equipped kitchen, glass doors open from the spacious living room to private pool and tropical landscaped deck. One bedroom on the second floor, and another bedroom located on the third floor. With an estimated square footageof 2160. Corazon is one of the largest 2 Bedroom Vacation Rentals in Key West, especially in the Old Town District. Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 2 beds, 2.5 bathrooms
    • View Details
    Corazon/601 Angela Street
    Key West FL
    24.554856, -81.799969
  9. Frangipani on Vonphister

    Nothing evokes a tropical feeling quite like the Frangipani tree. Their sweet scent and sheer beauty make them universally loved and this custom Key West vacation home is no different. Frangipani on Von Phister is a two-level contemporary home tucked away in the heart of the Casa Marina, steps from the beach. If you’re interested in spending a month or more in Key West, then you will want to live here. This property is perfect for families or couples traveling together looking to enjoy all aspects of Key West living. The Casa Marina location provides privacy and entertainment; it is 3 short blocks from the beach and tennis courts (tennis rackets available at the home as well as pool towels). Duval Street is just a short bike ride away, where you will surely discover colorful and charming shops and visit Mallory Square to pick up a locally made Key West gift (one bike provided at the home). Behind lush landscaping, the private residence has rolling gates able to fit two cars. The award winning architectural home is inviting and warm. You will feel comfortable entering the grand foyer with tall ceilings, high-tech lighting, a seating area and specifically curated art. The first floor is open, with marble floors, an ample entertaining area, a full office with printer, full laundry room, two spacious bedrooms, and a living and dining area with a large and functional kitchen. The impeccably detailed, gourmet kitchen has top of the line appliances, breakfast bar, and utensils/kitchenware for every occasion. The marble is decadent and clean, filled with possibilities. The dining area and the living space are a truly relaxing. Newly upholstered white furniture accented with peacock blues makes this casual, elegant beach-style home, inviting and serene. Floor to ceiling windows allow sunlight to fill the home. A large cable television, DVD player, DVDs, board games, and books allow your stay to be uniquely yours! Off the living room, sliding glass doors reveal outstanding tropical landscaping, a large pool with a great water feature and several outdoor seating areas throughout the property. Prepare for a magical stay of sun-filled days and expect for it to be hard to leave this inviting home. The two bedrooms on the first floor are slices of paradise boasting all modern amenities you could hope for. The ‘Mermaid’ room consists of two twin day beds, ensuite full bathroom, a wall mounted television and sliding doors to the front of the house. The second bedroom is as fully equipped with a queen bed, full ensuite bathroom, wall mounted television and sliding doors leading to the backyard. There is nothing like sliding open doors to welcome in the tropical paradise! A large marble staircase leads to the master suite fit for royalty. The spacious open concept area overlooks the whole house and has added amenities you would not believe. King sized bed with lush linens, a lounging area with a newly upholstered sofa chair and inlet shelving with books for your cool down periods. His and hers full bathrooms do not compromise a hint of elegance or privacy with closet space in both, a jet tub, and a 6-head shower; all desired ways to wind down. A luxurious private balcony only accessible from the master suite includes an outdoor shower, an orchid garden, and two lounge chairs. Enjoy the nature you see from this balcony while previewing the sunset and experiencing the tropical breeze. At night, look at the stars and take a shower in the warm night’s air. Frangipani on Von Phister is an experience we are sure you will enjoy and look forward to returning to again and again. Amenities: Gated, private residence featuring a sunny private (heat optional) pool and beautiful lush landscaping around the yard and several sitting areas. Fully equipped gourmet kitchen, granite countertops, breakfast bar, stainless steel appliances, private office with printer, alarms in all bedrooms equipped with USB port, full laundry room with washer/dryer and cleaning supplies, WIFI, cable television, DVDs, board games, tennis rackets, beach towels, grill, 2 off street parking spaces, central AC, ceiling fans, curated art from around the world, outdoor shower, balcony, full ensuite bathrooms. Read more »
    • Key West, FL
    • Casa Marina
    • vacation rental
    • 3 beds, 3 bathrooms
    • View Details
    Frangipani on Vonphister
    1020 Vonphister
    Key West FL
    24.550039, -81.7888
  10. Golf Villa - 20 Golf Club Dr

    Relax and enjoy your own bright and charming two bedroom, two bath, well maintained bungalow. The first floor offers an open floor plan, fully equipped kitchen, washer/dryer and spacious living room. Sliding glass doors open onto a covered patio where you can sit back, relax and enjoy the views of the Golf Course. Both second floor bedrooms have en suite bathrooms and one of the bedrooms has a balcony that looks out onto the front of the property. The Key West Golf Club is a gated community with 24 hour security, surrounded by tropical landscaping, also featuring a Rees Jones designed golf course, 2 pools, and a club house w/ fitness center. Tennessee Williams Fine Art Center, Lower Keys Medical Center, Old Town Key West, full service marinas, beaches, shopping, and dining are all just a short drive away. Estimated square footage for home is 900 sqft. Amenities: Fully Equipped Kitchen Washer/Dryer Access to Two Community Pools Central A/C Cable TV DVD player Telephone Upstairs balcony, front and rear covered porches Internet Read more »
    • Glenwood Canyon
    • Key West Golf Club
    • vacation rental
    • 2 beds, 2 bathrooms
    • View Details
    Golf Villa - 20 Golf Club Dr
    Key West FL
    24.576011, -81.739772
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305-294-3040 | homeskw@bellsouth.net | http://www.preferredpropertieskeywest.com | 520 Southard Street, Key West, FL 33040