Beachfront Rental Homes in Key West

Dreaming of a toes-in-the-sand vacation in the tropics? How about sipping an umbrella-studded drink and gazing out to sea from the comfort of your own terrace? Or being lulled to sleep each night by the rhythm of the sea? Historic Key West Vacation Rentals has the place for you! 

In Key West, you’re never far from a stunning view. And with an average of 260 days of sunshine a year, you’ll enjoy a front-row seat for sunsets off your deck, panoramic ocean vistas, the wonder of the island’s natural beauty and the tranquility that comes from the sighing sea. When you choose a beachfront Historic Key West Vacation home, you’ll claim the beach as your backyard. You’ll be steps away from staking out your place in the sand, novel in hand. Here in Key West, you’ll find unlimited opportunities for swimming, snorkeling, paddle boarding, fishing or simply lounging — all practically right outside your door. 

Consider, too, the privacy your own rental home affords, versus the commotion of a hotel. In a vacation rental property, you’ll enjoy space for spreading out in a private retreat, or the opportunity to share with family members and friends. You can cook in a gourmet kitchen, dine alfresco and enjoy quiet moments by the water. Plus, you’ll be in the middle of island action, where fresh seafood, local markets and restaurants beckon. Or grill your own catch of the day and enjoy it in the privacy of your own backyard. Whether you’re planning a beachfront family reunion, a celebration or an intimate, romantic getaway, Historic Key West Vacation Rentals has you covered. You’ll be immersed in the best of island life close to the beach.

Here’s a preview of some of our most popular properties on or right near a sandy shore — all waiting for you in beautiful Key West:

● Azur Palm: Spend a month in paradise at Azur Palm, an amazing 2BR, 2BA oceanfront home, and you’ll be stunned by seas of blue! Off the entry hall is a stunning white kitchen with tray ceiling, upgraded appliances, and quartz countertops. The kitchen affords sea views and overlooks the dining area with seating for a family of six. A wall of sliding doors gives way to an oceanfront balcony with a dining table, a large sofa and loungers. The primary king bedroom features balcony access for morning coffee. This luxurious home places you near the White Street Pier, Higg’s Memorial Beach Park and the Key West Nature Preserve.

● The Escape at Sunset Key:Have you ever daydreamed about spending time on a small private tropical island? Follow your heart, and spend an extended vacation in The Escape at Sunset Key, a 2BR, 3BA monthly rental on a secluded island just offshore from Key West. Relax and unwind as you feel the soft breeze on your face and your tensions melt away. Just a 5-minute ferry across calm waters, Sunset Key is a 27-acre residential neighborhood that will make you feel miles away from everything. Enjoy car-free, traffic-free living, outdoor amenities (pool, tennis courts) and witness the most beautiful sunsets on earth!

● Miss Sunshine: Can you think of a more perfect place to soak in the sun than at the aptly named Miss Sunshine? Situated just two blocks from the White Street Pier, this 3BR, 3BA home is within walking distance of Higgs Beach, the best place in Key West for an ocean swim. Here, you’ll spend 28 or more languid days around your private pool surrounded by lush foliage and Brazilian teak decking. Eat alfresco at your backyard dining table. Heck, there’s even an outdoor shower. You can stroll the beach in the mornings, work remotely during the day by your private pool surrounded by lush foliage and soak in the magic of Key West each night.

● Sea Vista: Do you dream of wiggling your toes in the sand or sipping coffee on your dock along The Keys? Look no further than Sea Vista, featuring a lush backyard that leads out to the warm waters of the Gulf of Mexico, where you can launch a paddle board or shallow-draft fishing boat. This lovely 3BR, 2.5BA home offers several outdoor areas that include a dining table, loungers, and covered porch with comfortable furnishings. Just close your eyes, breathe in the salt air, exhale and repeat!

● Seas The Day: Harry Truman’s Winter White House notwithstanding, if you’re longing for a weeklong seaside retreat, look no further than Seas The Day. This fabulous 2BR situated in the island’s premiere gated waterfront community in the Truman Annex is your vacation dream home away from home. You’ll find a waterfront park and playground, as well as Zachary State Park with its white-sand beaches and glimmering waters. And a short walk leads to a plethora of shops, restaurants and bars.

● Copa Cabana: Nestled between the Southernmost Point of the United States and the Hemingway House, Copa Cabana, a cozy 2BR home in Bahama Village is yours for a month! Key West’s gorgeous beaches beckon with shimmering waters, ivory sand and endless sunshine. Enjoy a drink in the evening in your jetted cocktail pool, lounge on the furnished wood deck, or engage in a little people- watching from the traditional front porch.