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Looking for a tropical escape with a unique island vibe? Our monthly rentals in Key West, Florida, offer the perfect mix of relaxation, adventure, and charm. From iconic sunsets to lively cultural events, Key West is an idyllic destination for extended stays, whether you're planning a seasonal retreat or a long-term getaway
Key Amenities
About this property
Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem!Step back in time and experience Old Key West charm in this delightful 2-bedroom Cigar Maker's Cottage, built in the 1880s. Nestled at 1008 Whitehead Street, the cottage sits just across from where a bustling cigar factory...
Key Amenities
About this property
This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....
Featured review
We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...
Key Amenities
About this property
Enjoy the ocean views from this beautifully appointed condo in the exclusive Key West Beach Club.This two-bedroom, two and half-bath waterfront condo that has been newly renovated with casual furnishing and all the comforts of home: central air conditioning, cable TV, washer/dryer, Wi-Fi, and a fully-equipped...
Key Amenities
About this property
Very good location in Big Pine, deer paradise, a very quiet place to relax and rest if what you want is incredible peace to relax, believe me, this is your place, lots of outdoor space, the house is on a corner, very cozy inside and out, outdoor hammocks, many places to sit and spend a lovely afternoon...
Key Amenities
About this property
TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!ENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street....
Featured review
Wonderful home, amazing response for any needs, great pool and parking. The covered porch (lanai) expanded the living space. We had an all around great experience. We will be back in the future!
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Key Amenities
About this property
Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As...
Explore a variety of monthly rentals in Key West, including historic homes, beachfront condos, and private cottages. Whether you’re seeking serenity or excitement, you’ll find the ideal rental to match your lifestyle. Enjoy the comfort and convenience of a long-term stay in the heart of the Florida Keys.
Don’t wait to secure your long-term rental in Key West. Browse our listings to find the perfect property for your stay. Whether you’re planning a winter retreat or a summer adventure, Key West offers endless opportunities to relax and explore.
It’s never too early to book your next getaway. Reserve your spot in advance to secure the best rental for your preferred dates, whether for a seasonal retreat or a long-term escape.
Group-Friendly Rentals: Traveling with family or friends? Key West offers spacious rentals with private pools and large living areas, perfect for group vacations or reunions.
Romantic Retreats for Couples: Key West’s sunsets, vibrant nightlife, and luxury accommodations make it an ideal spot for couples seeking a romantic getaway.
Winter Retreats for Snowbirds: Escape the cold and enjoy warm weather, turquoise waters, and the laid-back lifestyle of Key West for your extended stay.
Secure your winter retreat in Key West by booking one of our monthly rentals today. Embrace the luxury, sunshine, and vibrant island lifestyle that make Key West a favorite destination for snowbirds and long-term visitors
💰 Highest rates
January and February
🎉 Busiest month
March
🏠 Popular home types
Historic homes and waterfront cottages
🔥 Hottest months
July and August
❄️ Coldest months
January and February
☔ Rainiest months
June through September
🌺 Best months for flowers
April and May
🌴 Peak tourist season
January through March
🍂 Quietest months
September and October
🌊 Best beach months
April through June
🏌️ Best golfing months
November through April
🎨 Top cultural events
Fantasy Fest (October), Hemingway Days (July)
🍽️ Best dining months
January through March
🦋 Best months for nature activities
March through May
🛶 Best water sports season
June through September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
January through March
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