Find Christmas hotel deals in Islamorada

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Featured Christmas hotel deals in Islamorada

Top Islamorada Hotel Reviews

Find out more about Islamorada

Enjoy a warm Christmas vacation in Islamorada

Escape to Islamorada for a warm Christmas vacation. The winter season, from December to March, offers pleasant weather for exploring local attractions like Islamorada Brewery & Distillery or the MoradaWay Arts & Cultural District. Many properties provide amenities such as outdoor pools, firepits, and free bicycles, perfect for a relaxing holiday getaway.

Islamorada hotels for a Christmas vacation

December in Islamorada offers boat cruises and sunset experiences, alongside local breweries, a cultural district, and museums. The featured hotels provide comfortable places to stay while enjoying a warm-weather holiday.

Casa Morada
This hotel in Matecumbe offers a relaxing holiday escape with a balcony and bay views from your room. Travelers give it a guest rating of 9.4 out of 10.
  • Other amenities: You can enjoy ecotours and massage services, and a minibar is available in your room.
  • Neighborhood: Matecumbe
  • Nearby attractions: Islamorada Brewery & Distillery (about a 5-minute walk), Keys History & Discovery Center (about a 5-minute walk), Matecumbe United Methodist Church (about a 10-minute walk)
Hadley Resort and Marina
Located in Matecumbe, this resort provides a comfortable stay with air conditioning and barbecue grills, along with a firepit for cooler evenings. It has a guest rating of 7.6 out of 10.
  • Other amenities: Bike parking is available, and you can use concierge services or enjoy a free grab-and-go breakfast.
  • Neighborhood: Matecumbe
  • Nearby attractions: Islamorada Brewery & Distillery (about a 5-minute walk), History of Diving Museum (about a 10-minute walk), Florida Keys Brewing Co. (about a 25-minute walk)
Drop Anchor
This property offers a comfortable stay for your winter vacation with barbecue grills and air conditioning. Travelers give it a guest rating of 8.6 out of 10.
  • Other amenities: You can enjoy a resort view, and some rooms feature a separate bedroom or extra beds.
  • Nearby attractions: Founders Park (about a 5-minute drive), Rain Barrel Village (about a 5-minute drive), Islamorada County Park (about a 5-minute drive)
Coconut Cove Resort and Marina
This resort is a good choice for travelers seeking a warm holiday with a fitness center and barbecue grills. It has a guest rating of 9 out of 10.
  • Other amenities: The property includes a marina, and you can enjoy a free breakfast or use a free extra futon.
  • Nearby attractions: History of Diving Museum (about a 5-minute drive), Islamorada Brewery & Distillery (about a 5-minute drive), Founders Park (about a 5-minute drive)
Islander Resort
In the Matecumbe neighborhood, this resort offers a bar and air conditioning for a comfortable holiday stay. Travelers give it a guest rating of 9.4 out of 10.
  • Other amenities: The resort provides an airport shuttle, electric car charging stations, and free rollaway beds.
  • Neighborhood: Matecumbe
  • Nearby attractions: Keys History & Discovery Center (about a 5-minute walk), MoradaWay Arts & Cultural District (about a 15-minute walk), Hurricane Monument (about a 20-minute walk)

Frequently Asked Questions

What amenities should I look for when booking hotels for Christmas in Islamorada?

When booking hotels for Christmas in Islamorada, look for amenities that offer relaxation and comfort during your holiday stay. Consider properties that provide a jetted bathtub or a hot tub for unwinding. Some hotels also offer options like a deep tissue massage to enhance your vacation experience.

What is the weather like in Islamorada at Christmas?

In Islamorada during December, travelers can expect comfortable weather. Daytime highs are typically in the 70s to 80s Fahrenheit, making it a pleasant time for a Christmas vacation.

What types of food can I find in Islamorada during a Christmas trip?

During a Christmas trip to Islamorada, travelers can find a variety of food options. The area offers European cuisine, with choices like Mediterranean and Italian dishes. Seafood is also a prominent option for dining. Mediterranean is a dominant cuisine type available.

What are some places to visit in Islamorada during a Christmas trip?

For a Christmas trip to Islamorada, travelers can visit Anne's Beach or a beach near Islamorada. Other places to explore include the MoradaWay Arts & Cultural District, the historic ruins of Indian Key Historic State Park, and the History of Diving Museum.

What are the best hotels to stay in Islamorada for Christmas?

For a Christmas stay in Islamorada, consider several properties. Casa Morada, a 3.5-star hotel in Matecumbe, has a 9.4 out of 10 guest rating and offers rooms with a balcony. Hadley Resort and Marina, also 3.5 stars and located in Matecumbe, provides air conditioning and has a 7.6 out of 10 guest rating.


Drop Anchor is another option, a 3-star property with an 8.6 out of 10 guest rating. This hotel provides air conditioning for comfort during your visit.

Are there family-friendly hotels in Islamorada for Christmas travel?

Yes, Islamorada offers family-friendly hotels for Christmas travel, with several properties providing free cribs for younger travelers.


Fisher Inn Resort & Marina, a 3.5-star motel with an 8.2 out of 10 guest rating, also has games for children and beach toys. The 4-star Islander Resort, with a 9.4 out of 10 guest rating, is located in Matecumbe.


Also in Matecumbe, La Siesta Resort & Villas is a 4-star resort that earns an 8.6 out of 10 guest rating and provides free cribs.

Are there hotels for Christmas in Islamorada with a hot tub?

Yes, several hotels in Islamorada offer hot tubs for travelers during Christmas. The 3-star Coconut Cove Resort and Marina provides a private indoor hot tub and has a guest review score of 9 out of 10. Cheeca Lodge & Spa, a 5-star resort in Matecumbe, features a private outdoor hot tub and earned a 9.2 out of 10 guest rating.


The Caribbean Resort, also located in Matecumbe, offers a hot tub. This 3.5-star hotel has a perfect guest review score of 10 out of 10.

Are there hotels for Christmas in Islamorada near the Florida Keys Brewing Co.?

Yes, several hotels in Islamorada are near Florida Keys Brewing Co. The 3-star Sunset Inn, with a 9.2 out of 10 guest rating, is about a 15-minute walk away. Pines & Palms Resort, also 3 stars and rated 9.2 out of 10, is about a 25-minute walk from the brewery. For a shorter trip, the 4-star Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, which has a 9 out of 10 guest rating, is about a 5-minute drive from Florida Keys Brewing Co.

Are all taxes and fees included in the prices shown for in Islamorada on Expedia?

Yes, with Expedia’s upfront pricing you can compare in Islamorada, see what you’ll pay before booking, and choose the right stay for your trip. Whether you’re planning a family vacation or a premium escape, clear pricing helps you plan your trip with ease.

Can I cancel my booking for on Expedia?

Yes, you can—many Expedia hotel reservations offer free cancellation, provided that you cancel before the hotel's cancellation deadline. This is often within 24–48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's “Fully refundable property” filter during your search to find the right in Islamorada.

Can I find Expedia discounts for in Islamorada?

To look for discounts on in Islamorada, join One Key™—our free travel rewards program. One Key members get instant discounts with Member Prices and can earn OneKeyCash™* on eligible bookings. You can also save by bundling your hotel and flights together on Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Can I save money by booking flights and in Islamorada as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build a travel package. *Savings vary and are not available on all flight and hotel bookings.

How much does it cost to book in Islamorada?

Prices for in Islamorada vary, but you can find deals from $114 on Expedia. To find great prices, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to find our lowest rates.