18 Places To Be Home Away From Home In Key West

Here are 18 places to be home away from home in Key West.  Sometimes, you just have to leave home to feel at home. There's no better time to leave your home blanketed by snow, sleet, cold rains and almost no sunshine for warm, sunny, fresh, historic and beautiful Key West. Come for nightly, weekly and monthly getaways this winter when our conch island has the highest warm temperatures and sunshine of anywhere in the continental U.S.A. Come stay and play.  Work and learn. Earn and return every time you need a break.  Our brand standards include complimentary Internet, a full range of amenities, enhanced cleaning protocols and relaxed, easy feel-at-home settings. Most of our boutique luxury homes have heated pools and many are pet-friendly, too.  Where will you feel at home? Let's take a look.

Casablanca Too is the perfect vacation rental for two in sunny Key West. This is a spacious vacation rental with the added bonus of off-street parking and a private hot tub! Beautifully manicured grounds along with the wonderful outdoor areas set this property apart from others. Pack your wags. Small dogs are welcome here. too.

Casablanca - Nightly Rental 1 Bedroom 1 Bath Sleeps 4

This is a spacious, pet-friendly vacation rental that comes with the added bonus of off-street parking and a private heated pool! Casablanca is the perfect Key West vacation rental for those seeking a good time, but who would like to stay a distance from all the Duval Street excitement! 

Horse Conch is located upstairs on the second story and can be accessed by the stairway on the side of the building. It includes a shared, covered balcony that overlooks the sparkling pool and courtyard area. 

Petite Maison is a designer Key West Guest Cottage that is located in the Gallery District of Duval Street. This is a charming, tasteful, designer two-story cottage that is all-new, yet the cottage has all the charm of a traditional Key West home. The furniture is all updated and modern. There is parking for one car, however, you will not need a car when staying at Petite Maison. It's just a few blocks away from the Southernmost Beach, night clubs, and tourist areas. It's a quick safe walk to everything Key West has to offer. This cottage also allows for one dog guest, as well. 

Rooster Conch includes a shared, covered balcony that overlooks the sparkling pool and courtyard area. The inside of the unit offers adorable Key West decor throughout with colorful furnishings. 

This newly updated first-floor condo is located in the Shipyard section of the Truman Annex facing Southard Street. The Shipyard has an extra-large pool for its guests to enjoy with plenty of lounge chairs for you to work on your tan. Park your car in your dedicated parking space and leave it for the duration of your stay.

"Solaris Pair-A-Dise" allows couples traveling together to stay close, but also have their own private living room and kitchen. The unit allows for one dog as a guest and is located on a tiny lane and is a perfect and spacious retreat for up to four adults. Experience Blue Heaven, Martin's, 7Fish, Antonia's Italian, and all the good things Duval Street has to offer. Mallory Square is a 5-minute bike ride for those fabulous sunsets. 

Inn Cogneato is a newly renovated beautiful pet-friendly home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence, this home is perfect for a couple that plans on entertaining visiting guests or family during their stay. The brand new saline pool measures 14 x 8 feet, is 5 feet deep, has an in-pool bench for sitting. This pool is heated in season and has a beautiful custom waterfall! There is a patio and propane grill for grilling your Key West catch of the day!

This adorable pet-friendly gingerbread cottage with an amazing front porch is full of India Hicks’ Bahamas-meets-Britain inspired décor by famous designer Elizabeth Demos, and a very Key West-inspired indoor/outdoor living option with pocket doors and exposed beams that lead directly from the living area to the outdoor deck. The amazing heated pool is right off of the kitchen for easy entertaining day or night. There is mature tropical foliage with lots of seating areas and an electric grill for grilling your catch of the day! A fully-fenced yard is perfect for your Lemonade Furmaids as well! There is off-street parking for one car.

Experience hotel-like 5-star luxury but with the exclusive privacy of this adorable Key West home. This super cute home boasts all the amenities you would expect from a luxury hotel including a concierge and high-speed Wi-Fi. The first-floor French doors open to the private heated dip pool, covered lanai dining area, and ultra-comfy shaded outdoor lounge area. 

Fair Winds at the Foundry is a gorgeous coastal. immaculate, light and airy end unit townhouse in the Foundry section of the Truman Annex. Walking distance to ALL that Key West has to offer! This is a private, gated community that's close to beaches and state parks, as well as Old Town’s bustling restaurants and nightlife. The condo pool is located half a block away. There is a dedicated covered parking space for one car.

When you walk into the living room, you’re just a few steps from the pool with its custom waterfall. The expansive French doors can be left open to make the most of those tropical breezes. Drive into your private rocked driveway and find parking for two vehicles. Your stay at Southard Comfort would not be complete without enjoying the private outdoor shower. You can start your day with a relaxing shower under the tropical morning sun or end your day showering under the evening stars. It is also perfect for rinsing off the beach sand or ocean salt.

Historic Chavez House is a two bath two story eyebrow house on the National Register of Historic Places. It's newly renovated and very well appointed with fine linens, gorgeous furniture, ultra-comfortable mattresses, and a cool and calming color palette. Enjoy a dip in the new private pool and work on your tan on the large exterior deck! Chavez House also welcomes one dog guest.

Poinciana Garden (downstairs) and Poinciana Treetop (upstairs) at pet-friendly Poinciana Place are cozy and casual one-bedrooms that sleep up to 4 people each. Each kitchen has a full-size refrigerator and a small 4 burner gas stove, blender, microwave, and a toaster. Each living room has a queen sleeper sofa, television with cable, and free wifi. Other great amenities include free parking for one mid-size car per unit and an on-property bicycle rack for locking up your bicycles.

When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find yourself in the private brick courtyard facing the home with its French doors and balconies. As soon as you see the beautiful black bottom pool with a waterfall, the clamor of Duval Street will seem miles away as you prepare to luxuriate in this completely renovated and modern home.  Park your car in the off-street parking spot provided, and you’ll never need to drive it at all during your stay.

This is a pet-friendly, designer home with a brand new interior, re-using the Dade County Pine for the walls and floors, so the house has all the charm of a traditional Key West home. The bathrooms, kitchen, furniture, mattresses are all new. There's a large courtyard with a private heated saline pool and covered lanai. There is parking for one car.

Steamplant 208 is a two-level, 5 Star luxury residence with breathtaking panoramic views of Key West. Amenities include a private rooftop terrace with an elevated pool, a parking garage, private elevators for each residence, and it's pet-friendly. Traveling by yacht? The residences at the Steamplant offer boat slips that can accommodate vessels from 19 feet to 195 feet. 

The Truman Suites offers five separate fully equipped suites just a few steps from famous Duval Street. The two-story complex offers 7 bedrooms, 5 bathrooms and sleeps up to 18. The Truman Suites collection includes 1-2 bedroom suites — Harry, Margaret, Martha, Bess Suites, and John Truman's Hideaway. These suites can be booked individually as well as grouped. There is a brand new shared 14' x 10' heated pool with a tranquil waterfall feature! There are also loungers for being poolside. Beach towels provided.

These are 18 places to be home away from home In Key West. Sometimes, you have to leave your home to feel at home. Historic Key West Vacation Rentals is looking forward to welcoming guests to Key West. We want you to know we are doing our part in preventing the spread of COVID-19 in our community and workplace.  

Best of all, we're here to welcome you home to our homes!