Key West is unlike any place you’ll ever see. Why not see it the right way? Awake to dazzling daybreaks and wind down with sensational sunsets in your own private paradise. Many of our vacation rentals offer sweeping balconies and airy floor plans so you can enjoy the island view.
Living like a local doesn’t just happen on land. That’s why most of our Key West vacation homes come with a private boat slip. So you can accent your escape with fishing adventures, snorkeling expeditions or deep dives for dinner. Or just dock your boat and soak in the sunset.
Key West is a unique and different place. Shoes and schedules are shunned here. Which is why we accommodate different lengths of stays. From weekend getaways to month-long immersions, our flexibility is practically unheard of in this part of paradise. Let us know exactly what you want, and we’ll make it happen.
White Glove Service
Come unwind with us, and discover an immersive and all-inclusive experience that’s every bit as remarkable as your location. Want a fresh meal delivered to your door? Need your laundry cleaned? Curious about local hangouts? Our “white glove” concierge service gives you whatever you want. Whenever you need it.
Renew & Refresh
There’s something special about your own private oasis. Most of our Key West vacation rentals feature an expansive pool. So you can wash off from your ocean adventure. Or just chill by the water with a fresh drink. Whatever your style, we’ll provide you with plenty of beach towels and sun rays.
Our spacious homes are both modern and charming. Enjoy full kitchens, expansive balconies and wide-open rooms. Enveloped in lush natural surroundings. From bachelorette parties to weddings, from family vacations to corporate retreats, we offer something for everyone. All accented and elevated by a higher level of personal service.
Area GuideVIEW ALL
If it involves fun in the sun, pro tips on how to mix in with the locals, a recommendation for some tasty neighborhood eats or anything that would make your stay with us the very best travel experience you’ve ever had, you can find it here!
Spending A Month In Key West Like A Local
A month in Key West. Can you think of anything dreamier? There’s something in the air that makes this laidback, bohemian island so intoxicating. Perhaps it’s the big, bright blue sky with cumulus clouds floating lazily above palm trees, conch cottages and the endless spread of the Atlantic Ocean and Gulf of Mexico from all sides. Whatever it is, the quality of life on the island is dialed way up. If you’re lucky enough to retreat to Key West for a month (or an entire season), here are a few tips for long term living on island time.
Family Friendly Key West Vacation Guide
If you’re traveling to Key West with the whole family, you’re in luck! While it may have a reputation for its raucous nightlife, this southernmost island is an excellent destination for a family vacation. With exciting activities both on and off the water, casual restaurants and budget-friendly diversions like a day at the beach, it’s easy to keep a family of all ages entertained and happy on a Key West vacation. Read on for a family friendly Key West vacation guide.
Planning The Ultimate Key West Bachelor/Bachlorette Party
Key West is a prime destination for bachelor and bachelorette parties. There’s nightlife. There’s water sports. There’s delicious restaurants. And best of all, anything goes! Bond with your bros or connect with your gals and get a little wild in Key West before you get hitched with this guide to planning the ultimate Key West bachelor/bachelorette party.
Must See Sights in the Florida Keys
Key West has a surprisingly quirky and fascinating history that lives on today in historic sites and attractions around the island. Once the summer retreat of President Harry S. Truman, his Little White House has been preserved as a museum and event space inside the picturesque Truman Annex residential neighborhood.
IMPORTANT: You may have seen ads on Airbnb or Craigslist that appear to be about our properties or seem to have been placed by us. Please note that Key West Vacation Homes does NOT advertise on either Airbnb or Craigslist – and your response to any fraudulent “ad” for a Key West Vacation Homes property on either of these sites is NEVER received by us. These are fake ads run by scammers who have NO intention of honoring your reservation. All of us here at Key West Vacation Homes take pride in the security of all our guests. To further protect your valuable personal and financial information and ensure you are renting and communicating with Key West Vacation Homes, contact us directly by phone, email, or via our HomeAway listings.
Please note: 30 night minimum stay required on some homes due to a City of Key West ordinance and not negotiable.