Key West — Traveler Guide
Staying longer than a weekend? These Key West properties specialise in making extended stays feel like home — with fully equipped kitchenettes, in-unit laundry, generous living spaces, and weekly rates that won't break the bank. Ideal for remote workers, relocations, and leisurely explorations.
Quick Answer
Staying longer than a weekend? These Key West properties specialise in making extended stays feel like home — with fully equipped kitchenettes, in-unit laundry, generous living spaces, and weekly rates that won't break the bank. Ideal for remote workers, relocations, and leisurely explorations.
6 hotels reviewed · Price range: $, $$, $$$ · Last updated March 2026
About This Guide
Key West offers exceptional options for travellers seeking long stay hotels, and we've curated the very best. Each property has been selected for its outstanding facilities, prime location, and the quality of experience it delivers. Leading our list, The Almond Tree Inn excels with its exceptional attention to detail and commitment to the long stay experience. Cypress House Hotel offers a compelling alternative with its unique approach and distinctive character. Whether you're a first-time visitor to Key West or returning for another stay, these hotels represent the gold standard for long stay accommodation in the city. Each has been independently evaluated for quality, location, and value.
Insider Tips
Negotiate rates directly with the hotel for stays over 14 nights — they often beat online prices.
Check if utilities and WiFi are included in quoted weekly/monthly rates.
Ask about loyalty programme benefits for extended stays — some offer free upgrades.
Request a unit near laundry facilities for maximum convenience.
Our Picks
6 hotels · Updated February 2026
Midtown
A gracious Victorian guesthouse on White Street that balances Old Town proximity with slightly lower prices than the Duval Street corridor — 16 rooms arranged around a swimming pool under century almond trees. The owners' knowledge of Key West is encyclopedic and their morning fruit breakfasts are legendary among repeat visitors.
Old Town
A magnificent 1888 Conch Republic Classic House listed on the National Register of Historic Places, with wraparound verandas, a clothing-optional pool area, and 18 rooms that retain genuine period character. The location on Caroline Street puts Sloppy Joe's, the Ernest Hemingway Home, and the Historic Seaport a five-minute stroll away.
Old Town
One of Old Town's best-priced boutique options — a restored 1895 Conch House with 13 rooms, a plunge pool, and free beach cruiser rentals, all two blocks from Duval Street. The genuine B&B warmth, owner-operator hospitality, and extraordinarily central location make it one of Key West's best values.
Key West Harbor
A modern boutique resort on the harbor designed with a zero-waste philosophy — solar panels, electric boat charters, and a marine conservation partnership — without sacrificing any luxury amenity. Three pools, a water sports center, and 96 rooms with harbor views make it Key West's most thoughtfully conceived newer property.
New Town
Key West's largest hotel delivers a reliable Marriott experience with a private beachfront, rooftop infinity pool, full-service spa, and 220 rooms at prices that undercut Old Town equivalents by 30-40%. Ideal for families who want resort scale and water access without the Old Town premium.
South Beach
Key West's most family-friendly full-service resort, straddling Atlantic and Gulf beaches at the island's southern tip with three pools, a poolside tiki bar, and direct access to both Southernmost Beach and the Atlantic. The rooms in the Beach House are the finest, with private balconies facing the water.
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Common Questions
Most properties featured here include kitchenettes with a refrigerator, microwave, and stovetop at minimum. Full kitchens with ovens and dishwashers are available at many aparthotels.
Weekly and monthly rates are standard for long-stay properties, often 20-40% less than the nightly rate. The longer you stay, the better the rate typically becomes.
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Prices and availability change daily. Lock in the best rate by booking early — most of our top picks offer free cancellation.
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