The 8 BEST Key West Hotels for Christmas Stays 2026

Delivers a festive beachfront escape in the heart of Key West. Imagine celebrating the holiday season with your toes in the sand and a beautiful ocean view right outside your window. At Southernmost Beach Resort and Guesthouses, the vibrant atmosphere wraps around you, perfectly complementing your Christmas spirit. Enjoy oceanfront dining that transforms every meal into a special occasion, or rejuvenate with soothing spa services that melt away the stress of the season. This is where holiday memories are made, so don't hesitate, reserve your spot in this tropical paradise today.

Delivers breathtaking ocean views and a private beach for a truly magical Christmas escape. Imagine sipping hot cocoa on your private balcony as the sun sets over the sparkling waves. At The Reach Key West, the festive spirit comes alive with a stunning 137-metre private beach just steps away, inviting you to stroll along the shore or build sandcastles in the warm sun. Unwind by the outdoor pool or indulge in rejuvenating spa treatments that whisk you into a world of relaxation. This holiday season, let the enchanting atmosphere of Key West elevate your celebration, book your stay now and experience the magic.

Delivers a luxurious beachfront experience that transforms your Christmas getaway into a tropical paradise. Imagine celebrating the holiday season with the soothing sounds of the ocean and the warm sun kissing your skin. At Casa Marina Key West, you can unwind at the oceanfront pools or indulge in rejuvenating spa treatments, making every moment feel like a gift. Just a short drive from the vibrant Duval Street, you'll find the perfect blend of relaxation and island adventure. This Christmas, treat yourself to a magical stay that will leave you longing to return.

Brings the holiday spirit to life with its festive atmosphere and inviting poolside gatherings. At the DoubleTree by Hilton Grand Key Resort, the warm holiday vibes resonate through every corner, making it a prime choice for family celebrations. You can bask in the sun by the pool, sipping seasonal cocktails while the kids splash around joyfully. With an on-site restaurant that caters to festive cravings, every meal feels like a special occasion. This is where your Christmas in Key West truly comes alive, so don’t wait to secure your stay.

Brings Christmas cheer to life with a vibrant tiki bar and an inviting outdoor pool. Picture yourself unwinding at the tiki bar, sipping a festive cocktail while holiday lights twinkle above you. Just minutes from the lively Duval Street and the serene Key West International Airport, this hotel places you effortlessly at the heart of seasonal festivities. After a day of exploration, dive into the outdoor pool or soak in the hot tub, soaking up the warm Key West sun. This is the holiday getaway you've been dreaming of, secure your stay now and make this Christmas unforgettable.

Features a vibrant sun terrace and inviting outdoor pool for a festive Key West Christmas experience. Imagine sipping a cocktail at the pool bar while soaking up the warm sun, surrounded by the cheerful ambiance of Key West. The outdoor pool beckons you to unwind, offering a refreshing escape after a day of exploring the island. With a free shuttle to Old Town, every charming shop and delightful restaurant is just moments away, allowing you to embrace the holiday spirit fully. Don’t miss out on creating unforgettable memories, book your stay at Blue Flamingo Resort now.

Brings the holiday spirit to life with stunning sunset views and luxurious relaxation. Each evening, your private balcony invites you to witness the brilliant hues of the sunset, creating a magical atmosphere for the festive season. With three outdoor swimming pools, you can unwind and soak in the sun while sipping a cocktail, making every moment feel like a celebration. Indulge in culinary delights at Starboard restaurant, where holiday flavors come alive in a vibrant setting. The Marker Key West Harbor Resort is your gateway to an unforgettable Christmas escape, so don’t wait to make this seasonal dream a reality.

Features a heated pool overlooking the ocean for an unforgettable holiday escape. Imagine celebrating Christmas under the warm sun, lounging by the heated pool while the gentle waves serenade you. The inviting atmosphere at Hampton Inn Key West transforms your holiday into a tropical retreat, where you can enjoy poolside dining with breathtaking ocean views. Each non-smoking room, complete with a balcony, allows you to unwind in comfort, perfectly complementing your festive getaway. Don’t wait, book your stay now and immerse yourself in the magic of a Key West Christmas.