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 32 Holiday Resorts
1800 Atlantic, All Florida Keys Property Management
Spend any holiday in beautiful Key West for a unique getaway. Whether it's spring, summer, fall, or winter, the Florida Keys offer an unrivaled... more
- Beach
- Family
- Nature
- Fishing
- Romantic
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
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
- Beach
- Nature
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- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
Key West Bed & Breakfast
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
- Romantic
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
- Island
The Inn on Fleming
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
- Nature
- Romantic
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
- Island
Whether it's a summer celebration or a winter retreat, Ambrosia Key West is an excellent destination for your holiday getaway. Townhomes and cottages... more
- Beach
- Nature
- Romantic
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
Westwinds Inn is the perfect destination for you and your sweetheart to celebrate Valentine's Day. With kids under 12 not allowed, it's the ideal... more
- Beach
- Romantic
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
Has your Christmas tree ever been a palm tree? If not, then for your next holiday getaway, celebrate on the shores of the beautiful Florida Keys. Rock... more
- Beach
- Family
- Reunions
- Wedding
- Nature
- Fishing
- Romantic
- Honeymoon
- Cabins, Cottages, and Chalets
- Holiday
- Island
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
- Beach
- Family
- Romantic
- Luxury
- Honeymoon
- Holiday
- Island
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
- Beach
- Family
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Cabins, Cottages, and Chalets
- Holiday
- Island
- Villas and Condos
Preferred Properties Key West is a great destination for your next holiday vacation. Come during Christmas, Valentine's, or the Fourth of July and... more
- Beach
- Family
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
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
- Beach
- Family
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
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
- Beach
- Family
- Meetings
- Reunions
- Wedding
- Nature
- Fishing
- Romantic
- Luxury
- Historical
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
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
- Beach
- Family
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Holiday
- Bed & Breakfasts, Inns
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
- Beach
- Family
- Reunions
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Historical
- Honeymoon
- Diving
- Holiday
- Island
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
- Beach
- Family
- Meetings
- Reunions
- Wedding
- Nature
- Fishing
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Health
- Diving
- Holiday
- Island
- Spa
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
- Beach
- Family
- Nature
- Romantic
- Pet Friendly
- Luxury
- Honeymoon
- Holiday
- Island
- Villas and Condos
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
- Beach
- Family
- Fishing
- Romantic
- Luxury
- Boutique
- Holiday
- Bed & Breakfasts, Inns
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
- Beach
- Family
- Reunions
- Nature
- Fishing
- Romantic
- Luxury
- Historical
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
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
- Beach
- Family
- Golf
- Nature
- Fishing
- Romantic
- Luxury
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos
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
- Beach
- Family
- Nature
- Fishing
- Romantic
- Ecotourism
- Luxury
- Honeymoon
- Diving
- Holiday
- Island
- Villas and Condos