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. Admiral's Quarters-115 Front St #103

    Monthly Rental Only Welcome to the Admiral's Quarters. This extra large two bedroom two bath condo is located in the Truman Annex, Key West's premier residential community in Harbour Place, situated on the Atlantic Ocean front. This unit offers breath taking water views overlooking the Marina and Cruise Ship docks. The Condo is located just two blocks from Duval Street and all of the Old Town Key West attractions. Minutes away from the historical Fort Zachery and Truman's little White House. These are the largest condo's in Truman Annex with one assigned covered parking spot which is not needed but available if needed. You can use the large balcony to sit in the sun, or watch the cruise ships, there is even a BBQ grill. A large Smart TV is in the living room while another Smart TV is in the master. Master en suite has a large soaker tub to relax in after a long day at the beach. If you want to cook while your here, the kitchen is stocked to cook your catch of the day! Read more »
    • Key West, FL
    • Truman Annex
    • vacation rental
    • 2 beds, 2 bathrooms
    • View Details
    Admiral's Quarters-115 Front St #103
    Key West FL
    24.5551, 81.78
  2. 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
  3. BELLA VITA/ 410 Catherine St

    Southern Charm/Monthly Rental Only 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. Monthly Rental Only 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
  4. 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
  5. Casa Blanca/907 Frances Street

    Casa Blanca/907 Frances Street Monthly Rental or 6 Month Rental (please call for pricing for 6 months or more) Come experience and stay at this Authentic1920's Key West Home. This little piece of heaven still has the original Dade County Pine through out the house. When you walk thru the front door you are welcomed into the quaint living room. The kitchen is a farmer style kitchen, vaulted ceilings with a banquette style seating for 4. The windows in the kitchen open out and gives the room a bright, airy feeling. There is additional dining and seating for 4 in the living room. The main house is a one bedroom, one bath home with a door that will lead you out to your own private fenced in yard. Enjoy your morning coffee in the side yard, or just relax with a book and watch the people stroll past. The cottage is located right outside the main house that has an additional Queen size bed and it's own bathroom. This cottage also has the original Dade County wood through out, along with vaulted ceilings.This is where the washer/dryer is located. This home is located in Old Town, close to Duval and the Historic Downtown Seaport. This is a monthly rental only, sorry no pets accepted. Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 2 beds, 2 bathrooms
    • View Details
    Casa Blanca/907 Frances Street
    Key West FL
    24.554856, -81.799969
  6. Casa Royal/1219 Royal St

    Monthly Rental Only 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

    Monthly Rental Only 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. 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
  10. Four Palms/903 Washington

    Monthly Rental- Lovely 2 story home is in the well respected neighborhood of Casa Marina. Walk into a large open concept living and dining room with seating up to 8 people, plus an additional seating for 3 at the counter top. Prepare meals for your friends with this well equipped gourmet kitchen and stainless steal high end appliances. This house boasts beautiful Plantation shutters and tile flooring through out the house. Open up the French doors to let the breeze in and enjoy the day out on the covered lanai or splash around in the private pool while enjoying a tropical drink. There is outdoor eating for four at the table. The bedrooms are located on the second floor. The master bedroom is large and spacious with lots of storage and a en suite bathroom. The guest bedroom is spacious with a queen size bed and access to the second floor balcony. A separate cottage is on the property and sleeps four. This cottage has one separate bedroom with en suite bathroom. Their is a sleeper sofa in the living room of the cottage along with another full bath. A small kitchenette is in the cottage with full refrigerator and wine cooler, but no stove. Amenities BBQ Grill On street parking Heated pool/Jacuzzi Excellent location Large outdoor living Read more »
    • Key West, FL
    • Old Town
    • vacation rental
    • 4 beds, 4.5 bathrooms
    • View Details
    Four Palms/903 Washington
    903 Washington Rd
    Key West FL
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305-294-3040 | rentals@preferredpropertieskw.com | http://www.preferredpropertieskeywest.com | 520 Southard Street, Key West, FL 33040