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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
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
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...
Distance to beach: 0.4 miles to Fort Zachary Taylor State Park
Key Amenities
About this property
Key West is just like the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street and Zachary Taylor Park ( do yoga on the beach, swim, snorkel, or hang hammocks between the palms). Walk to shops, restaurants,...
Key Amenities
About this property
Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor...
Featured review
I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described
Key Amenities
About this property
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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Key Amenities
About this property
Welcome to the cutest little Conch Cottage in the Florida Keys! Located in the Seaside Resort Community, only ten minutes to Key West! You won’t find a more affordable and comfortable location than this! The resort has not one, but two large pools, one that overlooks the open water! Other amenities...
Key Amenities
About this property
Spacious 2-Bedroom Condo with Ocean Views & Island ComfortsThis beautiful 2-bedroom, 2-bath condo offers a lovely view of the Atlantic Ocean and an extra-large floor plan with a slightly oversized private balcony—accessible from both bedrooms and the living room. It’s the perfect island...
Key Amenities
About this property
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
Key Amenities
About this property
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,...
Key Amenities
About this property
Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have...
Key Amenities
About this property
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...
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
Welcome to Parothdhideaway, where it’s always Five O’clock! Less than 10 minutes’ walk from Duval Street you will find this tropical island getaway. Find yourself on island time yet still having every amenity at your fingertips like a soaking pool hidden under the trees on the large...
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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