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Nothing says the holidays like palm trees and white, sandy beaches-- or they can, if you decide to take a vacation to the Florida Keys! The Ocean’s Edge Key West Hotel & Marina is located right on Stock Island, and is the perfect for holiday vacations. With its fully stocked marina, there is no shortage of things to do, with deep-sea fishing, parasailing, swimming, and diving! For those who want a little bit of everything, Rent Key West Vacations is one of the oldest rental vacation properties in the Key West, and has the best properties with modern amenities including fully equipped kitchens and private decks with panoramic views. The Coral Bay Resort offers a great escape from the bustle of city life and into your own tropical getaway, giving you the perfect holiday without any of the stress and with the charm of the Keys. Find your best holiday in the Keys today!

Showing 1-20 of 22 Holiday Resorts

Oceans Edge Key West Hotel & Marina

Key West, Florida, United States
$299
1-877-250-3908

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... more

Resort features:
  • Beach
  • Family
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Rock Reef Resort

Key Largo, Florida, United States
$115
1-866-405-6812

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... more

Resort features:
  • Beach
  • Family
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday

Coral Bay Resort

Islamorada, Florida, United States
$129
1-888-328-0454

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... more

Resort features:
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island

Barefeet Rentals

Key Largo, Florida, United States
$175
1-866-599-3095

Can you picture a better place to spend the winter than Florida? Book your next getaway today. Head to Barefeet Rentals and you can wake up each... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island

Rent Key West Vacations

Key West, Florida, United States
$150
1-866-980-7608

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... more

Resort features:
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Historical
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Luxury Rentals by At Home in Key West

Key West, Florida, United States
$175
1-877-695-2791

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... more

Resort features:
  • Beach
  • Family
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

The Gardens Hotel

Key West, Florida, United States
$359
1-866-806-8810

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... more

Resort features:
  • Beach
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island

Keys Holiday Rentals, Inc.

Islamorada, Florida, United States
$170
1-866-967-3004

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... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Vacation Homes of Key West

Key West, Florida, United States
$250
1-866-241-1140

Whether you're planning your next summer holiday getaway or looking to celebrate an upcoming holiday, Vacation Homes of Key West offers everything you... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday
  • Island
  • Villas and Condos

Parrot Key Resort

Key West, Florida, United States
$179
1-866-939-3715

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... more

Resort features:
  • Beach
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Tranquility Bay Beach House Resort

Marathon, Florida, United States
$279
1-866-452-5369

Plan your next holiday vacation on the shores of the Gulf of Mexico! Tranquility Bay Beach House Resort offers you a place to unwind, relax, and have... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Key West Vacation Rentals

Key West, Florida, United States
$169
1-305-296-9292

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... more

Resort features:
  • Beach
  • Family
  • Golf
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Pier House Resort & Spa

Key West, Florida, United States
$330
1.305.296.4600

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... more

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Health
  • Diving
  • Holiday
  • Island
  • Spa

Chesapeake Beach Resort

Islamorada, Florida, United States
$179
1-305-664-4662

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... more

Resort features:
  • Beach
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Historical
  • Honeymoon
  • Diving
  • Holiday
  • Island
  • Villas and Condos

Pegasus International Hotel

Key West, Florida, United States
$109
+1-305-294-9323

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:... more

Resort features:
  • Family
  • Holiday
  • Luxury
  • Romantic

Amara Cay Resort

Islamorada, Florida, United States
$169
1-305-664-0073

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... more

Resort features:
  • Beach
  • Family
  • Nature
  • Fishing
  • Romantic
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Diving
  • Holiday
  • Island

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... more

Resort features:
  • Beach
  • Family
  • Holiday
  • Luxury
  • Romantic
  • Villas and Condos

iTrip - Islamorada

Islamorada, Florida, United States
$115
+1 (866) 599-2369

Celebrate on the coast at any of these Florida Keys stays! When December rolls around, warm your heart and your skin when you swap the white snow for... more

Resort features:
  • Beach
  • Family
  • Golf
  • Romantic
  • Luxury
  • Honeymoon
  • Health
  • Holiday

The Inn at Key West

Key West, Florida, United States
$118
1-305-294-5541

The Inn at Key West offers a prime location to enjoy your holiday vacation! Or if you need a reason to celebrate check out the Fantasy Fest Key West.... more

Resort features:
  • Beach
  • Family
  • Nature
  • Luxury
  • Holiday
  • Villas and Condos

The Banyan Resort

Key West, Florida, United States
$190
1.866.371.9222

Escape the ordinary during the holidays and experience something truly unique. The Banyan Resort blends history with modernity for a special getaway... more

Resort features:
  • Beach
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Holiday
  • Timeshare
  • Villas and Condos

Showing 1-20 of 22 Holiday Resorts

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