Give thanks, island-style: Spend a family Thanksgiving in Key West

  • As the holidays approach, many of us dream about slowing down, spending quality
    time with loved ones, and reflecting on everything we’re grateful for. This year, why not
    trade the hectic pace and chilly weather for palm trees, ocean breezes, and family time
    in paradise? A Thanksgiving getaway to Key West is a unique way to celebrate
    togetherness while enjoying everything this beautiful island has to offer in the temperate
    fall and early winter months.
     
    A perfect pairing: Thanksgiving and Key West
    Thanksgiving is all about gratitude and connection — and in Key West, it’s easy to
    embrace both. From late October through early January, the island enjoys warm, sunny
    days and cooler, balmy evenings. Flights are convenient, the weather is ideal for a
    variety of outdoor adventures, and there’s a sense of calm that invites you to slow
    down, unwind, and focus on what truly matters: time with family.
     
    Your home away from home for the holiday
     
    Historic Key West Vacation Rentals offers a plethora of truly unique, lovingly restored
    historic homes that make hosting Thanksgiving a joy. Each property is thoughtfully
    designed for family gatherings, with everything you’ll need for your holiday away from
    home, including many of the following features:
    ● Well-equipped kitchens: Many of our properties feature fabulous kitchens, ideal
    for preparing a traditional holiday feast or trying your hand at fresh local seafood
    dishes.
    ● Expansive dining areas: There’s room for everyone to gather around the table
    to share stories, laughter, and gratitude for special time spent together.
    ● Comfortable living spaces with TVs: Lounge and gather for games,
    conversation, or watching football together on Thanksgiving Day.
     
    This Thanksgiving week, whether you prefer an intimate cottage or a spacious home
    with room for extended family, let Historic Key West Vacation Rentals help you find the
    perfect setting for creating lasting memories. Here is a short list of properties to
    accommodate your family for Thanksgiving week gatherings:
    ● Fair Winds at the Foundry : Your home Thanksgiving is a three-story
    townhouse flooded with natural light, vaulted ceilings and an open concept living area. This 2 BR, 2.5 BA beauty is in the exclusive and historic Truman Annex. Just steps away from the beach, your family can also enjoy all the action on Duval Street.
    ● Casablanca Grande : On the edge of Historic Old Town and tucked in a
    residential neighborhood, this 2BR home sleeps 6 and is a great place to enjoy
    both the fun and carefree vibes of Key West. This spacious rental includes
    access to a private 20-foot by 10-foot pool and hot tub.
    ● Serene Lily : Enjoy Thanksgiving week in this upscale 2BR, 2.5BA home located
    where the Gulf meets the Atlantic. It’s elegantly decorated and features
    sophisticated Serena and Lily touches throughout a space bathed with natural
    light. Enjoy alluring art and a serene ambiance that sets the stage for the family
    vacation of your dreams.
    Island-inspired ways to celebrate
    Beyond the meal, Thanksgiving in Key West offers a unique opportunity to enjoy
    endless ways to connect and enjoy your time together:
    ● Take a post-feast walk: Stroll through Old Town’s charming streets or head to
    Fort Zachary Taylor Historic State Park for a scenic beach walk and stunning
    sunset views.
    ● Explore nature: Rent bikes or hop in a golf cart for a family tour of the island, or
    venture out on the water for a snorkeling or sailing trip.
    ● Savor the season: Visit local farmers’ markets for fresh island produce, enjoy
    casual dining at waterfront cafés, or treat the family to Key Lime pie from an
    iconic bakery.
    The best time to visit Key West
    Fall and early winter are truly special in Key West. With fewer crowds, pleasant
    weather, and a laid-back vibe, it’s a season that encourages you to slow down and soak
    up the island’s tranquility. You’ll also enjoy seasonal events, vibrant sunsets, and all the
    island’s festive charm as the holidays approach.
     
    Make this Thanksgiving one to remember
    This year, let the sun, sea, and spirit of Key West bring your family together. Book a
    stay with Historic Key West Vacation Rentals and enjoy the perfect mix of home
    comforts, historic charm, and tropical beauty — all designed to help you focus on what
    matters most. Ready to plan your Thanksgiving escape? Explore our collection of
    unique historic homes and book your fall or early winter stay today at Historic Key West
    Vacation Rentals.

Published on Sunday, August 24, 2025

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