Key West Monthly and Seasonal Rentals are the perfect option for an extended stay in Paradise. Historic Hideaways offers numerous options to make your stay hassle-free and filled with the best that Key West and the Florida Keys have to offer. Monthly/Seasonal Rentals have 30 night minimums. Except for Jan - March, they are not restricted to calendar months. So your arrival or departure date can be any day of the month, so long as your reservation is for at least 30 nights. Please keep this in mind when selecting your dates to be sure you meet the minimum stay rule in order to bring up available options. (Due to strict City regulations, no exceptions may be made to the minimum stay.) Discounts are often available for monthlies, especially in off-season or if staying for multiple months…so please ask! Monthly/Seasonal rentals have a cap on utilities such as electric, water, and propane. Please see our FAQ page for other rules & items specifically related to Monthly/Seasonal vacation rentals.
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Experience paradise in sumptuous style. That's what Paradise Grand, a breath-taking yet comfortable five-bedroom, four-bath estate, is all about. The house and private grounds and off-street parking occupy a whole city block of historic Old Town, exceptional spaciousness on the small island of...
Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower. Five doors of...
Everyone and everything in Key West goes at its own speed, a wonderfully decelerated, human-friendly pace. Locals call it "island time." It's no accident that this beautifully restored 19th century home with four bedrooms and two full baths is named "Island Time" in honor of that...
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This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books,...
Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom, two-full-bath conch cottage in Old Town Key West. Recently restored and updated to include amenities such as a heated pool with rainforest waterfall, granite counter tops,...
Sun, fun, and relaxation are the mainstays of life on the little island of Key West. To enjoy this tropical haven for yourself, the first step is securing the right accommodations. If a single-family home with three bedrooms, two full baths, a sparkling private pool, two...
Looking for an ideal vacation? This charming three-bedroom, three-bath home is the perfect getaway spot. The style? A classic Key West eyebrow with two saw-tooth additions and plenty of Dade County pine. The story? The name "Maximo Cabana" commemorates Maximo Diaz, who bought the house in...
Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a...
Casa Angelina's covered, wrap-around veranda may be the first thing about this property that raises your heart rate above normal, but it won't be the last. Imagine yourself relaxing at the front to catch the street-side activity or cozying up on the side for privacy and...
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In addition, save 3% off final negotiated rates if you pay by check.
To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era...
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This three-bedroom, three-full-bath cottage exudes the kind of at-ease ambiance that tells you you're right where you need to be to have the best vacation ever. The cottage is in the Meadows neighborhood on the grounds of an impressive Key West estate. Like...
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Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most distinctive two bedroom/two bath homes. Located on fashionable Southard Street in the heart of Old Town, the first thing you notice as...
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So you've decided to become one of those lucky enough to be vacationing in extraordinary Key West this year! Your next step is to choose just the right residence. With two plus bedrooms, two full baths, and a stellar location, Azure Hideaway could...
En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern...
For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and modern functionality. The pool and...
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Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath condo is...
The pineapple-or ananas as it's known by its genus name-is the classic symbol of hospitality. This two bedroom, two full bath conch house, aptly named Ananas, is truly the embodiment of warm, welcoming hospitality. Its location, style, and comfort reward the lucky visitors who choose to...
The name of this home-Palm d'or-echoes the Palme d'Or, the highest award at the Cannes Film Festival. In this case, the award goes to the palm tree landscaping of this two-bedroom, two full-bath residence. The place is ringed in feathery palms, creating a perfectly secluded oasis...
Land's End is a charming one-bedroom cottage in Old Town, one block away from the Historic Seaport, a ten-minute walk to Duval Street and Mallory Square, and situated near some of the most architecturally beautiful houses on the streets of Key West. Location, location, location!
From...
The art of island living involves making efficient use of limited space. This charming first-floor, one-bedroom apartment does just that. It occupies the rear portion of an award-winning 1890s Victorian home on Solares Hill, the highest point of land in Key West. This quiet Old Town...
All you have to do is just show up. This cozy one-bedroom cottage has everything you need for your dream vacation. Inside the gated enclave, a large, heated, residents-only pool creates a visual centerpiece. It's easy to imagine yourself lazing in the shimmering turquoise water, on...
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Campbell Cottage is the perfect place for living large in an intimate, comfortable one bedroom/one bath cottage. A locked privacy fence surrounds the lushly landscaped Campbell Court compound, which has an enticing Monaco pool at its center. You can step off your front...
