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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
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Pool & Jacuzzi Resurfacing NoticePlease be advised that the pool and jacuzzi area will be closed for resurfacing beginning: July 6th – August 30th (weather permitting)The entire pool and jacuzzi area will be fully closed off during this time to allow the contractor to safely complete...
Featured review
Very thing was good the condo was perfect and the pool was great the parking was close to the elevator
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Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 AtlanticExperience comfort and elegance in this beautifully renovated 2-bedroom, 2-bath condo located in the prestigious 1800 Atlantic community. Each bedroom features a king-size bed, generous closet space, and direct access to a private balcony...
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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...
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Welcome to “The Coconut” – Your Slice of Old Town ParadiseTucked into the heart of Old Town Key West, The Coconut is your dreamy island hideaway — where history meets laid-back tropical living.Built in the late 1800s and full of classic Key West charm, this sun-drenched...
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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...
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Luxurious Renovated Monthly Rental at 1800 Atlantic – Ocean Views & Premium Comfort Step into elegance at this beautifully renovated, high-end condo at 1800 Atlantic. From the moment you enter, you'll appreciate the meticulous attention to detail and modern upgrades throughout the space. Enjoy...
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Charming Pool Cottage in the Heart of Old Town Key WestPerfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated...
Distance to beach: 2 miles to Smarthers Beach and Higgs Beach
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This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and dining...
Featured review
Sunshine House on Harris Street, Key West is a Home away from Home. We enjoyed 2 months of comfort and convenience at this home. The home is furnished with tasteful Island Decor. The layout is 3 bdrms...
Distance to beach: 0.4 miles to Fort Zachary
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Escape the winter and settle into this beautifully renovated 2-bedroom, 1-bath condo in the heart of Old Town Key West — perfect for snowbirds and monthly renters seeking the ideal balance of tranquility and convenience. Located in the prestigious gated community of Truman Annex at the Shipyard...
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When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you...
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Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...
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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...
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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