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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 29 Holiday Resorts

Oceans Edge Key West Resort & Marina

Key West, Florida, United States
$199
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
  • Meetings
  • Reunions
  • Wedding
  • 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
  • Ecotourism
  • Honeymoon
  • Cabins, Cottages, and Chalets
  • Holiday

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

Keys Holiday Rentals, Inc.

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

Whether you're looking to get away 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
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Island
  • Villas and Condos

Coral Bay Resort

Islamorada, Florida, United States
$129
1-855-533-0216

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

The Inn on Fleming

Key West, Florida, United States
$250
1-305-294-4043

Whether you're looking for a getaway over the Fourth of July or Valentine's Day, the Inn on Fleming is an ideal destination for your Florida vacation.... more

Resort features:
  • Nature
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns
  • Island

Tranquility Bay Beach House Resort

Marathon, Florida, United States
$279
1-855-604-1305

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 Bed & Breakfast

Key West, Florida, United States

Start a new holiday tradition at the Key West Bed & Breakfast! Whether you're looking for a place to celebrate New Years or Valentine's Day, this... more

Resort features:
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns
  • Island

Westwinds Inn

Key West, Florida, United States
$135
1-305-296-4440

This is the perfect destination for your and your sweetheart to celebrate Valentine's Day. With kids under 12 not allowed, it's the ideal setting for... more

Resort features:
  • Beach
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

Mermaid & Alligator Key West

Key West, Florida, United States
$148
1-305-294-1894

Whether you're looking for a place to celebrate the Fourth of July or a warm retreat over Christmas, the Mermaid & Alligator Key West is the... more

Resort features:
  • Beach
  • Nature
  • Romantic
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

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

Florida Keys Vacation Rentals Inc.

Key West, Florida, United States
$200
1 (305) 743-5181

Celebrate the winter holidays in the beautiful Florida Keys! With Florida Keys Vacation Rentals, you can enjoy a warm and and sunny beachside vacation... more

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

Luxury Rentals by At Home in Key West

Key West, Florida, United States
$175
1-305-296-6996

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

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

The Gardens Hotel

Key West, Florida, United States
$359
1-305-294-2661

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

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

The Cabana Inn

Key West, Florida, United States
$209
1-305-296-2323

Beat the winter blues and escape to The Cabana Inn! Instead of snow, enjoy white sandy beaches with a backdrop of crystal blue water when you relax on... more

Resort features:
  • Beach
  • Family
  • Fishing
  • Romantic
  • Ecotourism
  • Luxury
  • Honeymoon
  • Holiday
  • Bed & Breakfasts, Inns

NYAH Key West

Key West, Florida, United States
$189
1-305-296-2131

Get away from the winter blues and head to Key West! Book a stay at Nyah Hotel and instead of shoveling your car out of the snow, you can pick up sea... more

Resort features:
  • Beach
  • Family
  • Fishing
  • Romantic
  • Luxury
  • Boutique
  • Holiday
  • Bed & Breakfasts, Inns

Barefeet Rentals

Key Largo, Florida, United States
$175
1-305-394-9787

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
  • Villas and Condos

Parrot Key Resort

Key West, Florida, United States
$179
1-888-211-0348

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

Showing 1-20 of 29 Holiday Resorts

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