Vacation Rentals & Apartments in Key West

Experience the ultimate tropical escape with vacation rentals in Key West, where laid-back island vibes meet sophisticated coastal luxury. This southernmost city in the continental United States offers an incredible collection of properties ranging from historic cigar cottages tucked along quiet lanes to beachfront condos with stunning ocean views. These distinctive accommodations feature classic Key West architecture with charming wraparound porches, coral stone foundations, and vibrant tropical landscaping that captures the essence of this legendary island paradise.

What makes vacation rentals in Key West truly special is their unique blend of modern amenities and authentic island character. Many properties were once artist havens or historic homes, now transformed into comfortable retreats that maintain their original charm while offering contemporary conveniences.

Vacation accommodation in Key West provides an intimate connection to local culture, with many properties located in authentic neighborhoods where guests can experience the genuine spirit of island life. Here are the amenities guests can expect when choosing these exceptional island retreats:

• Private heated pools and hot tubs for year-round relaxation
• Air conditioning systems to ensure comfort during warm tropical days
• Pet-friendly accommodations welcoming furry family members
• Private balconies and terraces with stunning water or garden views
• Dedicated parking spaces, a valuable commodity on this compact island
• Chef-quality kitchens equipped with Keurig coffee makers and gas grills
• Barrier-free accessibility features for all guests
• Lush tropical gardens creating private outdoor sanctuaries

Key West attracts diverse travelers seeking everything from adventure and culture to relaxation and romance. Beach lovers will discover pristine stretches like Smathers Beach and the crystal-clear waters of Fort Zachary Taylor Historic State Park Beach, perfect for swimming, snorkeling, and sunset watching. Food enthusiasts can explore the island's famous conch fritters, fresh seafood, and Cuban-influenced cuisine at legendary spots like Blue Heaven and El Siboney Restaurant. History buffs will be captivated by the Hemingway Home and Museum, the Truman Little White House, and the island's fascinating maritime heritage. Couples seeking romance will find vacation homes in Key West ideal for intimate getaways, with many properties offering private hot tubs and sunset views. The best time to visit is during the dry season from December through April, when temperatures hover around a comfortable 75-80°F (24-27°C), though this is also peak season with average weekly rental prices around $1,300 CAD. Spring and fall offer excellent value with temperatures in the mid-80s°F (29°C) and weekly rates dropping to approximately $1,000 CAD, while summer brings the warmest weather but also the highest humidity and occasional afternoon showers.

Discover the most captivating experiences this tropical paradise has to offer, from iconic landmarks to hidden gems that showcase the authentic spirit of island life.

1. Southernmost Point of Continental USA
2. Hemingway Home and Museum
3. Mallory Square Sunset Celebration
4. Key West Butterfly and Nature Conservatory
5. Fort Zachary Taylor Beach

Southernmost Point of Continental USA

Stand at this iconic landmark marked by the famous colorful buoy, representing the southernmost tip of the continental United States, just 90 miles from Cuba.

Hemingway Home and Museum

Explore the beautifully preserved Spanish Colonial estate where Ernest Hemingway lived and wrote, home to the famous six-toed cats that still roam the lush gardens.

Mallory Square Sunset Celebration

Join the nightly tradition of watching spectacular sunsets while enjoying street performers, local artisans, and the vibrant energy of Key West's most famous gathering.

Key West Butterfly and Nature Conservatory

Immerse yourself in a tropical paradise filled with hundreds of exotic butterflies, rare birds, and beautiful flowering plants in this climate-controlled sanctuary.

Fort Zachary Taylor Beach

Relax on Key West's most beautiful beach, featuring pristine white sand, clear turquoise waters, and excellent snorkeling opportunities within the historic state park.

Indulge in Key West's exceptional dining scene with these highly-rated restaurants that capture the island's unique flavors and atmosphere:

• Blue Heaven (4.6/5 stars) - A legendary spot serving Caribbean-inspired American cuisine in a colorful, bohemian setting where roosters roam freely and live music fills the air
• Kaya Island Eats (4.7/5 stars) - A modern island bistro offering innovative dishes with fresh, local ingredients and creative tropical cocktails in a stylish, contemporary atmosphere
• El Siboney Restaurant (4.6/5 stars) - An authentic Cuban restaurant beloved by locals for its traditional recipes, generous portions, and no-frills atmosphere that delivers genuine island flavors

Understanding Key West's unique character will enhance your island experience significantly. The island operates on "Key West time," a relaxed pace where flip-flops are acceptable everywhere and sunset watching is considered a daily ritual.

Local hosts consistently recommend exploring by bicycle, with Fury Water Adventures and Island Bicycles offering convenient rental services with pickup and delivery. For those preferring motorized transport, Minty's provides reliable scooter and golf cart rentals.

Pink Taxi offers affordable airport transfers, though many guests discover that vacation homes to rent in Key West are strategically located within walking distance of major attractions. The island's compact size means most destinations are accessible on foot, making it easy to stumble upon hidden gems like the White Street art gallery district or the authentic Cuban coffee at local cafes in the historic district. Sustainability-conscious travelers will appreciate that many properties offer digital keyless entry systems, reducing environmental impact while providing contactless convenience. Most accommodations welcome pets for around $25 per night, though weight restrictions typically apply. The island's diverse community creates a welcoming atmosphere where locals eagerly share fascinating Key West tales with visitors. For the ultimate experience, consider booking beachfront vacation rentals in Key West that provide direct access to pristine shores and unforgettable sunrise views over the Atlantic Ocean.