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Key West Hotels & Vacation Rentals for Christmas

Key West
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$100 - $199
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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

Condo Key West
Dec 19 - Dec 26
$270 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in Key West with Large Pool + Ocean View

4.7
Excellent (136 ratings)
Key West, Monroe County, Florida, United States
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Resort Key West
Dec 19 - Dec 26
$443 per night
Resort ∙ 6 guests ∙ 3 bedrooms

Lovely Resort in Key West with Outdoor Pool

3.8
Good
Key West, Monroe County, Florida, United States
Free cancellation
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House Key West
Dec 19 - Dec 26
$620 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Key West with Private Balcony + Ocean View + Close to Beach

4.7
Excellent (55 ratings)
Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$375 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Key West with Pool & Yard, Close to Mallory Square

4.8
Outstanding (56 ratings)
Key West, Monroe County, Florida, United States
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Accommodation Key West
Dec 19 - Dec 26
$378 per night
Accommodation ∙ 2 guests ∙ 1 bedroom

Rental in Key West with Pool, Yard & Patio, Next to Duval Street

4.4
Very good (930 ratings)
Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$341 per night
House ∙ 2 guests ∙ 1 bedroom

Vacation Home in Key West with Free Parking, Near Key West Tropical Forest & Botanical Garden

4.4
Very good (10 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Dec 19 - Dec 26
$373 per night
House ∙ 4 guests ∙ 1 bedroom

Pleasant Vacation Home in Key West with Free Parking, Near Key West Tropical Forest & Botanical Garden

5.0
Outstanding (2 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Dec 19 - Dec 26
$539 per night
House ∙ 3 guests ∙ 1 bedroom

Pleasant Vacation Home in Key West with Free Parking, Close to Key West Tropical Forest & Botanical Garden

Key West, Monroe County, Florida, United States
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House Key West
Dec 20 - Dec 27
$1,551 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Key West with Pool, Grill & Yard

5.0
Outstanding (1 rating)
Key West, Monroe County, Florida, United States
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Where to Dine for Christmas in Key West

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

House Key West
Dec 19 - Dec 26
$383 per night
House ∙ 4 guests ∙ 1 bedroom

House in Key West with Pool

4.6
Excellent (68 ratings)
Key West, Monroe County, Florida, United States
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Cottage Key West
Dec 19 - Dec 26
$533 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Beautiful Cottage in Key West with Private Pool, Next to Southernmost Point + Beach Nearby

4.5
Excellent (51 ratings)
Key West, Monroe County, Florida, United States
Very popular
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Apartment Key West
Dec 19 - Dec 26
$327 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Key West with Private Parking, Close to Mallory Square

4.6
Excellent (188 ratings)
Key West, Monroe County, Florida, United States
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Studio flat Key West
Dec 20 - Dec 27
$223 per night
Studio flat ∙ 2 guests ∙ 1 bedroom

Studio in Key West with Private Patio, Near Southernmost Point

4.5
Excellent (5 ratings)
Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$527 per night
House ∙ 2 guests ∙ 1 bedroom

Lovely House in Key West with Onsite Pool, Next to Key West Tropical Forest & Botanical Garden

4.0
Very good (2 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$1,771 per night
Condo ∙ 14 guests ∙ 4 bedrooms

Condo in Key West with Free Parking + Water Views

5.0
Outstanding (11 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$447 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Key West with Grill, Yard & Pool, Next to Mallory Square

4.6
Excellent (118 ratings)
Key West, Monroe County, Florida, United States
Very popular
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Resort Key West
Dec 19 - Dec 26
-35%
$550
$356 per night
Resort ∙ 127 guests ∙ 3 bedrooms

Resort in Key West with Patio, Pool & Yard

4.1
Very good
Key West, Monroe County, Florida, United States
Free cancellation
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House Key West
Dec 19 - Dec 26
$3,143 per night
House ∙ 20 guests ∙ 10 bedrooms

Pleasant House in Stock Island with Botanical Garden

4.8
Outstanding (90 ratings)
Key West, Monroe County, Florida, United States
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Best Holiday Attractions in Key West

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

Studio flat Key West
Dec 19 - Dec 26
$274 per night
Studio flat ∙ 2 guests ∙ 1 bedroom

Studio in Key West with Private Parking, Close to Mallory Square

4.5
Excellent (5 ratings)
Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$539 per night
House ∙ 2 guests ∙ 1 bedroom

House in Key West with Private Parking, Next to Key West Tropical Forest & Botanical Garden

4.1
Very good (24 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Dec 19 - Dec 26
$455 per night
House ∙ 2 guests ∙ 1 bedroom

Charming House in Key West with Private Parking, Next to Key West Tropical Forest & Botanical Garden

4.3
Very good (16 ratings)
Key West, Monroe County, Florida, United States
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Apartment Key West
Dec 20 - Dec 27
$384 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Key West with Pool & Grill, Close to Mallory Square

4.7
Excellent (130 ratings)
Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$597 per night
House ∙ 3 guests ∙ 1 bedroom

Vacation Home in Key West with Private Parking, Near Key West Tropical Forest & Botanical Garden + Pool View

Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$423 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Key West with Pool, Close to Mallory Square

4.9
Outstanding (61 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$467 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo in Key West with Pool & Yard, Next to Southernmost Point

4.9
Outstanding (6 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Dec 19 - Dec 26
$551 per night
House ∙ 4 guests ∙ 1 bedroom

Wonderful House in Key West with Hot Tub & Grill, Next to Southernmost Point + Beach Nearby

4.4
Very good (87 ratings)
Key West, Monroe County, Florida, United States
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House Key West
Dec 19 - Dec 26
$359 per night
House ∙ 4 guests ∙ 1 bedroom

House in Key West with Jacuzzi & Grill, Next to Southernmost Point

4.4
Very good (150 ratings)
Key West, Monroe County, Florida, United States
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Things to Do With Your Family During Christmas Vacation in Key West

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

Villa Key West
Dec 19 - Dec 26
$820 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa in Key West with Private Balcony, Close to Mallory Square + Garden View

4.5
Excellent (29 ratings)
Key West, Monroe County, Florida, United States
Very popular
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House Key West
Dec 19 - Dec 26
$567 per night
House ∙ 6 guests ∙ 2 bedrooms

Beautiful Vacation Home in Key West with Private Balcony, Next to Mallory Square

5.0
Outstanding (36 ratings)
Key West, Monroe County, Florida, United States
Very popular
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Condo Key West
Dec 19 - Dec 26
$439 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Elegant Condo in Key West with Pool, Near Southernmost Point

5.0
Outstanding (66 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$390 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Key West with Private Parking, Next to Mallory Square

4.6
Excellent (92 ratings)
Key West, Monroe County, Florida, United States
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Apartment Key West
Dec 19 - Dec 26
$331 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Bahama Village with On-Site Parking, Next to Southernmost Point

5.0
Outstanding (3 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$604 per night
Condo ∙ 5 guests ∙ 2 bedrooms

Condo in Key West with Private Balcony, Near West Martello Tower + Ocean Views

4.8
Outstanding (101 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$276 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Key West with Pool, Near Southernmost Point + Tropical Views

4.6
Excellent (126 ratings)
Key West, Monroe County, Florida, United States
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Cottage Key West
Dec 19 - Dec 26
$532 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Lovely Cottage in Key West with Yard, Close to Southernmost Point + Close to Beach

4.7
Excellent (43 ratings)
Key West, Monroe County, Florida, United States
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Condo Key West
Dec 19 - Dec 26
$410 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo in Key West, Near West Martello Tower + Next to Beach

4.7
Excellent (167 ratings)
Key West, Monroe County, Florida, United States
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Information about Key West Hotels & Vacation Rentals for Christmas

😎 Least busy month June
🥳 Busiest month September
🛏️ Popular home types Apartment rental and House rental
🌡️ Hottest months 89 °F in August and July
❄️ Coldest months 65 °F in January and February
🌧️ Rainiest months September and August

Frequently Asked Questions

What types of vacation homes are available for Key West Hotels & Vacation Rentals for Christmas?

You can browse 1,293 House rental and 189 Apartment rental for Key West Hotels & Vacation Rentals for Christmas right here on HomeToGo.

Key West Hotels & Vacation Rentals for Christmas: How much does a stay cost?

You can get a great vacation home for somewhere between $488 and $1,232 and find discounts up to 60%!

Can I find a vacation rental for a group of guests for Key West Hotels & Vacation Rentals for Christmas?

in Key West, large groups should look for House rental since they usually fit 7 people.

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Average Nightly Rental Prices in Key West

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Vacation Rental Price Information in Key West

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Rental availability information in Key West

Key West Hotels & Vacation Rentals for Christmas Inspiration

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