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Showing 1-20 of 22 Holiday Resorts

Pier House Resort & Spa

Key West, Florida, United States
Compare
$330

Get away from the snow during the holiday season with a family trip to Pier House Resort & Spa in Key West. Bask in the sun, while everyone else you know is shivering! You can jump right in with Danger Charters or Sunset Watersports whose experts will get you set up for many types of water recreation. Enjoy the island life with a poolside bar,... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 142 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Health
  • Diving
  • Holiday
  • Island
  • Spa

Hawks Cay Resort

Duck Key, Florida, United States
79
Very Good
2221 Reviews
Compare
$299

Start a new holiday tradition at the luxurious Hawks Cay Resort. Located on the island of Duck Key, Hawks Cay is the perfect place to get away from it all no matter what holiday you might be celebrating. Take in the refreshing tropical atmosphere and the calming sounds of the waves as you lounge on the beaches. Explore the life underwater on a... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 420 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Duck Key
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Golf
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Health
  • Diving
  • Holiday
  • Island
  • Spa
  • Villas and Condos
  • Waterpark

Chesapeake Beach Resort

Islamorada, Florida, United States
77
Good
706 Reviews
Compare
$179

Escape winter and head to the Florida Keys for your next Christmas or Thanksgiving vacation! Rather than fighting the crowds at the mall, enjoy 700 miles of beach with a good book. Take a diving adventure instead or go for a fishing cruise to enjoy Labor or Memorial Day. No matter what the holiday, Chesapeake Beach Resort is the perfect... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 65 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Islamorada
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Oceans Edge Key West Hotel & Marina

Key West, Florida, United States
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Holiday retreats can take place any time of the year, over Christmas, New Years, or during Spring Break when the kids are out of school. Explore the wonders of Stock Island as you enjoy the miles of soft beaches and the exciting waters of the Gulf of Mexico and Atlantic Ocean. The full-service marina allows you to enjoy everything from deep-sea... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 175 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico and Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Coral Bay Resort

Islamorada, Florida, United States
Compare
$129

Escape the winter and head to Islamoranda and stay at Coral Bay Resort for your next holiday vacation! Instead of stressing at the mall during Christmas, sip a margarita on the beautiful sandy beaches! Coral Bay Resort is the perfect destination for a romantic Valentine's Day as well. No matter when you come, you'll have the time of your life at... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 17 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Islamorada
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island

Key West Vacation Rentals

Key West, Florida, United States
Compare
$169

Not a fan of the cold winter months in the northern states? There's no better escape than the pinnacle of US topicality, Key West. Have Christmas on the beach in a swimsuit, and wave at Santa as he flies over with his shades on. Let everyone else deal with the cold- you're on vacation, after all!... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 207 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island

Rock Reef Resort

Key Largo, Florida, United States
82
Very Good
341 Reviews
Compare
$115

Has your Christmas tree ever been a palm tree? No? well maybe you should try celebrating your holiday traditions along the shores of the beautiful Atlantic Ocean! Rock Reef Resort presents luxurious accommodations with stunning views and thoughtful amenities. Enjoyable outdoor and onsite activities all year-round. Perfect for any holiday!... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 21 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key Largo
  • Nearby Water Atlantic Ocean/Florida Bay
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday

Luxury Rentals by At Home in Key West

Key West, Florida, United States
Compare
$175

Start a new holiday tradition on the shores of Key West! This beautiful island retreat lets you and your family, friends, or significant other enjoy the wonders of the Atlantic and a laid-back tropical experience while you celebrate the holidays. Whether you spend your time on the beach, explore the underwater world, or just bask in the views from... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 100 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Atlantic Ocean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Nature
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Rent Key West Vacations

Key West, Florida, United States
Compare
$150

Why not spend a holiday in a special location that has a little bit of everything? Rent Key West Vacations has the perfect places for you to spend a quiet Christmas or a crazy Fourth of July. If you want to just relax, or you're looking for the best local action, Rent Key West Vacations is the place to find either one for a holiday you'll never... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 85 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Caribbean
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Historical
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
Compare
$170

Whether you're looking to getaway over the cold winter months or planning a vacation to celebrate a holiday, Keys Holiday Rentals provides you with everything you need for a memorable stay. Their premier rentals are located throughout the Upper Keys area and put you just minutes from all the action. Reconnect with friends or family while bike... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 35 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Islamorada
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

La Jolla Resort Hotel

Islamorada, Florida, United States
Compare
$149

Whether you're here to celebrate the winter holidays or planning a trip over the summer holiday when the kids are out of school, La Jolla Resort Hotel provides you with everything you need for a fantastic time. Comfortable accommodations look out over Florida Bay and are equipped with modern touches for your convenience, while the onsite pool and... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 21 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Islamorada
  • Nearby Water Florida Bay
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

The Gardens Hotel

Key West, Florida, United States
95
Excellent
387 Reviews
Compare
$359

When it comes to spending the holiday in Key West, there's no place better than the Gardens Hotel. Their luxury accommodations and wide array of amenities puts them above the rest in terms of comfort and convenience. You can enjoy a complimentary breakfast to start your day and spend your time exploring the wonders of the island! Go shopping on... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 22 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Parrot Key Resort

Key West, Florida, United States
Compare
$179

Beat those winter blues and take your holiday to the warm Florida sunshine! Lay out by one of the four swimming pools indulging in endless drinks from the Tiki Bar, rent a jet-ski or kayak for a fun water adventure, or test your luck on the nearby golf courses and tennis courts! With spacious accommodations and incredible onsite dining, everything... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 148 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Vacation Homes of Key West

Key West, Florida, United States
Compare
$250

Whether you're planning your next summer holiday getaway or looking to celebrate an upcoming holiday, Vacation Homes of Key West offers everything you need for a comfortable and memorable time. Their luxurious rentals ensure you have plenty of space, no matter if you're here with family, a group of friends, or just your sweetheart. Spend your days... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 59 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Tranquility Bay Beach House Resort

Marathon, Florida, United States
90
Excellent
627 Reviews
Compare
$279

Plan your next holiday vacation on the shores of the Gulf of Mexico! Tranquility Bay Beachhouse Resort offers you a place to unwind, relax, and have fun! Their charming accommodations with stunning ocean views, an onsite restaurant, and plenty of things to do from surfing and diving to sunbathing and sandcastle building, all come together to offer... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 106 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Key West
  • Nearby Water Gulf of Mexico
  • Open Dates All Year
RESORT TYPE(S):
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

KeysCaribbean

Marathon, Florida, United States

The holidays are the time to relax and celebrate with your loved ones and KeysCaribbean makes it easy to do just that! What better way to spend time with those who matter than on the shores of the Atlantic. Here, you can lounge on the beach with a drink, or head out and explore. Whatever you choose to do, you'll be sure to have an unforgettable... more

Amara Cay Resort

Islamorada, Florida, United States
$169

Make a little holiday magic in the island treasure Amara Cay Resort. Oceanic splendor lends its natural beauty to dreamy blue waters ripe with giant sports fish, Everglades National Park saltwater wilderness, and the seaside reefs, beaches, and wildlife that make this Florida Keys island village hotel a host for the best adventures.... more

Pegasus International Hotel

Key West, Florida, United States
78
Good
722 Reviews
$109

The Pegasus is the only Art Deco Hotel Located in the heart of downtown Key West, Florida and walking distance from all Key West's famous attractions: Ernest Hemingway's house, Margaritaville, and much more. Free parking, swimming pool, Jacuzzi, sun deck Dining, Gift Shop, Cigar Store, the Pegasus International Hotel has all the conveniences of a... more

The Reach Resort A Waldorf Astoria Resort

Key West, Florida, United States
80
Very Good
1598 Reviews
$179

Escape the ordinary during the holidays and experience a luxurious beachfront getaway at The Reach Resort! With the white-sand shores and clear blue waters just outside your door, it's the perfect destination. Enjoy a variety of activities such as snorkeling, sailing, surfing, and more!... more

The Banyan Resort

Key West, Florida, United States
86
Excellent
135 Reviews
$190

Escape the ordinary during the holidays and experience something truly unique. The Banyan Resort blends history with modernity for a special getaway you'll never forget. And minutes away you'll find all the fun activities that Key West is known for like boating, deep sea fishing and sailing!... more

Showing 1-20 of 22 Holiday Resorts

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