Key West Hotels & Vacation Rentals for Christmas

Key West
Anytime
2 guests

Go Tropical this Season with Key West Hotels for Christmas

Located on the southern tip of Florida, Key West experiences fabulous weather even in December and is a unique place to spend the holidays with all the family. The archipelago is packed full of attractions like the former house of author Ernest Hemingway and some of the best diving and snorkeling in the world. Add to this Christmas lights, decadent food, and festive shows and Key West vacation rentals for Christmas become simply one of the best ways to spend the holidays.

Christmas in Key West: Top Accommodations

House ∙ 4 guests ∙ 2 bedrooms
Stock Island, Monroe County, Florida, United States
from $83
VRBO
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House ∙ 4 guests ∙ 2 bedrooms
Stock Island, Monroe County, Florida, United States
from $80
VRBO
4.0
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House ∙ 4 guests ∙ 2 bedrooms
Stock Island, Monroe County, Florida, United States
from $80
VRBO
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House ∙ 6 guests ∙ 2 bedrooms
Stock Island, Monroe County, Florida, United States
from $80
VRBO
3.7
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House ∙ 4 guests ∙ 2 bedrooms
Stock Island, Monroe County, Florida, United States
from $80
VRBO
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House ∙ 4 guests ∙ 2 bedrooms
Stock Island, Monroe County, Florida, United States
from $80
VRBO
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Apartment ∙ 2 guests
Key West, Florida Keys, Florida, United States
from $216
VRBO
4.7
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Apartment ∙ 2 guests
Key West, Florida Keys, Florida, United States
from $289
VRBO
4.7
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Apartment ∙ 2 guests ∙ 1 bedroom
Key West, Florida Keys, Florida, United States
from $226
VRBO
4.6
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Where to Dine for Christmas in Key West

If you want to escape to Key West for some festive sun, you won't have to compromise on a traditional Christmas lunch. Tuck into hearty classics such as roast beer with potatoes or enjoy a seafood twist on firm favorites at the charming Matt's Stock Island.

  • 1. The Saint Hotel

    This charming boutique hotel serves up a traditional meal with all the trimmings in a relaxed, family-friendly environment. You can opt for a table just for you and your family or join a large table and celebrate the festivities with others. Reservations are strongly recommended.

  • 2. Mary Ellen's

    Mary Ellen's is famed for its classic comfort food of turkey with Guinness gravy, roast potatoes, and stuffing. Desserts are included and the casual atmosphere is great for those who prefer a laid back approach to Christmas rather than a refined affair.

  • 3. Matt's Stock Island

    The head chef at Stock Island, Kalen Fortuna, has created a truly exquisite festive menu which takes Christmas classics and gives them a coastal twist. Indoor and outdoor seating is available and the chic decoration is rustic but still smart. Along with stunning food and fabulous views, Matt's Stock Island makes for a magnificent place for an indulgent Christmas lunch.

Best Places to Stay for Christmas in Key West

Apartment ∙ 2 guests
Key West, Florida Keys, Florida, United States
from $146
VRBO
4.4
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House ∙ 4 guests ∙ 1 bedroom
Key West, Florida Keys, Florida, United States
from $164
VRBO
4.8
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House ∙ 2 guests ∙ 1 bedroom
Key West, Florida Keys, Florida, United States
from $103
VRBO
4.0
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Best Holiday Attractions in Key West

Key West Hotels for Christmas are the perfect choice for those who want to spend the holidays in the sunshine and make the most of the great outdoors. Enjoy wonderful outdoor attractions like the Conch Train which tours the festive lights of Key West and soak up the festive atmosphere at the opulently decorated Little White House.

  • 1. Lighted Boat Parade

    Weeks of preparation go into this fabulous light parade with locals decorating their vessels in a myriad of lights which culminates in a dazzling spectacle at Christmas. The procession starts at Schooner Wharf and then traverses the entire Key West Bight where you can enjoy the wonderful spectacle.

  • 2. Little White House

    This wonderful Key West museum is a must-visit during the holiday season. It was formerly a retreat for President Harry S. Truman and throughout the Christmas period it's wonderfully adorned with decorations and lights. It's also located in the picturesque Old Town which is superbly decorated throughout the season and a lovely place to spend some time.

  • 3. Conch Train Holiday Lights Tour

    This characterful train rides through the neighborhoods of Key West and is a wonderful way to see the town's decorations, both professional and amateur. Cooking and cider are also served prior to the tour's departure to add to the festive feel.

Recommended Accommodations for Christmas in Key West

House ∙ 2 guests
Key West, Florida Keys, Florida, United States
from $438
VRBO
5.0
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Apartment ∙ 2 guests
Key West, Florida Keys, Florida, United States
from $166
VRBO
4.7
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House ∙ 2 guests
Key West, Florida Keys, Florida, United States
from $287
VRBO
4.6
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Things to Do With Your Family During Christmas Vacation in Key West

Key West is a fantastic destination to spend the festive period with all the family. Enjoy charming seasonal performances like the magical Nutcracker or take a bike ride through the quaint streets of the Old Town and soak up the Christmas cheer.

  • 1. The Nutcracker

    Each year the Tennessee Williams Fine Arts Center produces a wonderful interpretation of The Nutcracker. They add a tropical twist on the classic and the show is bound to be a hit with the whole family. The center also stages a number of additional festive tributes including old-school Hollywood Christmas specials.

  • 2. Old Town Bike Ride

    The balmy temperatures mean taking a bike ride to see the festive displays in the Old Town is a pleasure even in December. The traditional sites are decked in gingerbread millwork and twinkling lights and some rental firms will even bring the bikes to your accommodation or hotel.

  • 3. Christmas Ultimate Adventure

    Add a little adventure to your festive trip with a visit to the beach for a fun-filled day of watersports and ride on a catamaran – the giant inflatable slides are a firm favorite with the kids.

Top Offers for Christmas in Key West

Apartment ∙ 2 guests ∙ 1 bedroom
Key West, Florida Keys, Florida, United States
from $244
VRBO
5.0
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House ∙ 4 guests ∙ 1 bedroom
Key West, Florida Keys, Florida, United States
from $278
VRBO
4.4
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House ∙ 4 guests ∙ 1 bedroom
Key West, Florida Keys, Florida, United States
from $528
VRBO
4.8
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The Weather in Key West

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- Rainy days

Average Nightly Rental Prices in Key West

Vacation Rental Price Information in Key West

Vacation Rental Availability in Key West

Rental Availability Information in Key West

Other Popular Destinations for Christmas