12 Places Key West Is Serving Up The Sunshine

Here are 12 places Key West is serving up the sunshine. You'll feel right at home among our locals and our other winter Snowbirds. One thing we all have in common is our love for our warm, Caribbean lifestyle, our delicious fresh seafood, the arts, entertainment and our easy, timeless way of life. Come with your family, your friends, or right by yourself. Stay and play. Work and learn. Watch and observe. It's winter in Key West and it's wonderful!

This is a spacious one-bedroom 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. Other great amenities include free parking for one mid-size car and it's pet-friendly!

Park your car in the off-street parking spot provided, and you’ll never need to drive it at all during your stay. There's a beautiful black bottom pool, plenty of loungers and outdoor spaces with seating. A majority of the tourist attractions are located here as well as numerous restaurants, shops and galleries. The neighborhood boasts historic homes, shotgun and conch style homes.

The Margaret Truman Suite is steps from Duval Street, the Lighthouse, Southernmost Point, the Hemingway Home, shops, restaurants, and art galleries! Enjoy the brand new shared heated pool with a tranquil waterfall feature! Bath linens are supplied as well as beach towels in a convenient tote.

Welcome to Poinciana Treetop, a sunny Key West vacation rental. This casual upstairs unit is located in the heart of Old Town Key West — less than 2 blocks from Duval Street and central to the island’s best attractions and things to do. Open the French doors from your bedroom and step out into the second-floor lanai. In the backyard, there is a shared gas grill, lush garden, back deck with chaise lounge chairs and outdoor dining set. Other great amenities include free parking for one midsize car, as well as an on-property bike rack for locking up your bicycles. Small dogs are welcome, as well.

This is a gorgeous coastal,  immaculate light, and airy end unit townhouse in the Foundry section of the Truman Annex. It's in a private, gated community. Close to beaches and the state park, 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.

This suite is furnished with a full kitchen, contemporary living room with comfortable furniture, new plush mattresses with premium linens, bathroom with Travertine shower, in-suite washer and dryer, high-speed Wi-Fi, flatscreen TVs in every bedroom, and a large flatscreen TV in the living room. There is a brand-new shared 14' x 10' heated pool with a tranquil waterfall feature! There are also loungers for relaxing poolside and beach towels are provided.

Small dogs are okay for this cozy and casual one-bedroom first-floor unit. Open the French doors from your bedroom and step out into the first-floor lanai, where your private hot tub awaits. The backyard features a shared gas grill, lush garden, back deck with chaise lounge chairs, and outdoor dining set. Other great amenities include free parking for one midsize car and an on-property bicycle rack for locking up your bicycles.

This is the historic and pet-friendly Chavez House on Margaret Street! Fine linens, gorgeous furniture, ultra-comfortable mattresses, and a cool and calming color palette. At 1415 sq ft this home comfortably sleeps 6. Enjoy a dip in the new private pool, work on your tan on the large exterior deck!

Located on a tiny lane in Old Town, this is a perfect and spacious retreat for one to two adults.  Open the doors from your bedroom and step out onto the side shared deck area under the giant Banyan tree. Step outside the kitchen door and you will find the infrared grill.

This a private detached one-bedroom modern studio cottage. It features top-of-the-line amenities and brand-new furnishings. Right outside is the 14' x 10' shared heated dipping pool with an amazing waterfall feature. Plenty of loungers for catching the Key West sun. Towels provided! 

This super cute home boasts all the amenities you would expect from a luxury hotel including a concierge and high-speed Wi-Fi. At the same time, you can live like a local by taking advantage of the fully equipped kitchen. Enjoy the privacy our tucked-away location affords smack dab in the middle of Key West’s oldest neighborhood. The first-floor French doors open to the private heated dip pool, covered lanai dining area, and ultra-comfy shaded outdoor lounge area.

Inn Cogneato is a newly renovated beautiful home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence, this pet-friendly 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! 

In a world where so many things are unstable, unclear and uncertain, Key West is one place where you are certain to have consistently warm weather, a slower pace, plenty of cultural and artistic inspiration and these 12 places Key West is serving up the sunshine. Find out more on our website or with our very sunny Vacation Planners!