Join Our Newsletter!

Sign up for our emails to get exclusive news, information and the best rates on your vacation!

Your island winter escape awaits: Rare seasonal availability on select Key West rentals


Winter in Key West feels like a secret you can’t wait to share. While much of the world bundles up, our island is glowing with golden sunshine, breezy blue skies, and palm-shaded streets alive with color and culture. December through March is the most magical island time — whether you’re craving a warm-weather holiday, a long-awaited January reset, or a mid-winter beach escape that puts joy back on the calendar.
 And the best part? A collection of our most sought-after homes still has availability this season — some for monthly stays, others for nightly or weekly getaways. Below, discover beautifully restored historic cottages, private-pool retreats, and spacious monthly rentals perfectly positioned near beaches, bustling Duval Street, world-class dining and sunset celebrations.
 If you’ve been dreaming of Key West this winter, this is your moment.

3920 1 B

DECEMBER GETAWAYS

La Casita en Cima
2 BR | 2 BA | Monthly Rental
Perched in a tranquil Old Town neighborhood, this elevated home blends modern coastal comfort with timeless Key West charm. It features bright interiors, a fully equipped kitchen, a breezy lanai and lush tropical landscaping that delivers vacation serenity from the moment you arrive. Guests love its easy stroll to neighborhood cafés and proximity to Duval Street without the noise. It’s the perfect December hideaway for relaxing, working remotely, or simply soaking in Old Town’s warm winter glow.
Copa Cabana
2 BR | 2 BA | Monthly
 Vibrant, playful and quintessentially Key West, this home is a favorite for couples or solo travelers who want to be close to everything. Located just steps from the Historic Seaport, this colorful retreat features tropical décor, sleek finishes, and a private outdoor patio perfect for morning coffee or sunset cocktails. It’s ideally situated for walk-everywhere convenience — waterfront dining, sunset sails, live music, and Duval Street are all within minutes.
Sea Vista
3 BR | 2.5 BA | Monthly
 For those seeking relaxation with a view, Sea Vista lives up to its name. This waterfront condo offers panoramic ocean scenery, airy interiors, and a private balcony where the sunrise feels like your own personal show. With access to a heated pool and the shoreline, it affords plenty of space to work, rest and play. Sea Vista provides a serene December escape just a short drive from Old Town’s lively streets, and dock access for a shallow draft, 21-foot maximum boat.

3921 2 B

DECEMBER & JANUARY ESCAPES

Palm Hideaway
3 BR | 2 BA | Monthly
 Tucked beneath stately palms and swaths of tropical greenery, Palm Hideaway is a peaceful retreat with enviable outdoor living spaces. Lounge by the heated pool, dine al fresco beneath the palms, or curl up in chic, airy interiors that feel like a boutique island hotel. Conveniently close to Old Town and near the Casa Marina area of Key West, guests can walk to Higgs Beach dog park or enjoy local restaurants and nightlife.
Blue Haven
4 BR | 3 BA | Monthly
 This attractive home with a private, bougainvillea-adorned gate and a fenced yard is one of Key West’s most in-demand winter retreats. This home blends relaxation and convenience effortlessly: spend your mornings swimming, your afternoons exploring Old Town, and your evenings dining under twinkle lights in the private courtyard. Its clean, stylish design and resort-like amenities make it ideal for families or groups traveling together.

3922 3 B

NEW YEAR WISH LIST

Seas The Day
2 BR | 1 BA | Monthly
 An updated first-floor condo in the gated Shipyard section of Truman Annex, Seas The Day puts you a short walk from Fort Zachary Taylor, Mallory Square sunsets and the waterfront while tucking you into a quiet, tree-lined community. The condo sleeps four, has an oversized shared pool, private patio with dining and gas grill, in-unit washer/dryer and a designated parking spot. Ideal for guests who want the best of Old Town while enjoying easy poolside living. Note: Monthly option begins January 2026.
Fair Winds at The Foundry
2 BR | 2.5 BA | Monthly
This bright, end-unit townhouse in the Truman Annex combines three levels of airy living, vaulted ceilings and multiple outdoor spaces. The primary suite (king) with private balcony joins a second ensuite bedroom (plus a living room sleeper sofa) to make it comfortable for groups up to six. Guests enjoy a shared pool, private fenced patio with grill, covered dedicated parking, washer/dryer, and a short stroll to waterfront attractions, Duval Street and Mallory Square. Note: Monthly option begins January 2026.
Sanctuary on South
4 BR | 3.5 BA | Monthly
This roomy Casa Marina-area home is perfect for longer stays and soaking up island life. This home accommodates up to eight guests and includes features such as indoor/outdoor living with pool access, a private pool, outdoor dining, washer/dryer and plenty of workspace. This property is a true monthly option—perfect for families or remote workers who want a full-service Key West base in a quieter, upscale neighborhood near the ocean.

3923 4 B

FEBRUARY & MARCH GETAWAYS

Flamingo Cottage
2 BR | 1 BA | Nightly/weekly
A new rental in Historic Old Town, this adults-only home features traditional Dade County pine walls, vaulted ceilings, a loft sleeping space, French doors that lead to the island sunshine, and a kitchenette suited to laid-back mornings. A restored cigar maker cottage, it has a lofted feel in parts, a front porch for morning coffee, AC, smart TV and is walkable to restaurants, galleries and Duval Street attractions. Note: This home is independently managed by Historic Key West Vacation Rentals.
Gardenia Cottage
2 BR | 1 BA | Nightly/weekly
 Originally home to artisan cigar workers, Gardenia is nestled down a gated walkway, but walkable to Duval Street, restaurants and bars. Wrapped in tropical plantings, it features a king and a queen bedroom (sleeps four), a private porch and access to a communal pool. The adults-only cottage features hardwood floors, a sunny living room with a skylight, loft sleeping above and a king bedroom leading to a private brick patio.

3925 5 B

Why winter in Key West?

Beyond the island’s sun-soaked weather and vibrant culture, winter here is truly special:
●       Perfect beach weather without the summer humidity
●       Outdoor dining morning to night
●       Sunset celebrations every evening at Mallory Square
●       World-renowned festivals, from food and wine to art and music
●       Water adventures — snorkeling, sailing, kayaking, eco-tours
●       A lively yet relaxed winter energy that feels restorative and joyful
 Whether you’re planning a month-long retreat or a sunny week between holidays, Key West offers an unbeatable winter escape — and our available homes make it easy.

Book before these dates disappear
 Availability during the island’s peak season is incredibly limited — and these openings won’t last long. Each of the properties above offers something uniquely Key West: historic charm, modern luxury, private pools, unbeatable locations, or serene monthly stays.
 Explore the listings, choose your retreat, and let Historic Key West Vacation Rentals help you plan your winter escape to the island where summer never ends.
Ready to book?  Visit Historic Key West Vacation Rentals to secure your winter getaway today.

  • Key West Chamber of Commerce Logo
  • Key West Business Guild Logo
  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
  • Florida VRMA Logo
  • VRMA Logo
  • AirBnB Super Host Badge
  • Vrbo Premier Host Badge
We use cookies to help us give you the best experience on our website. If you continue without changing your settings, we'll assume that you are happy to receive all cookies on our website. However, if you would like to, you can change your cookie settings at any time. Find out more.