A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Find Ski Hotels in Key West, FL from CA $729

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Key West Ski Hotels

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Key West ski hotels

A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A pathway through a lush garden with various plants and trees.
A living room with a sofa, armchair, coffee table, and a cabinet with decorative items.
A bar with a signboard listing various destinations.

1. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
CA $301
CA $742 total
includes taxes & fees
Oct 13 - Oct 14
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
A room with a dark blue dresser, a lamp, and a sign reading "OUR HAPPY PLACE".
A coastal residential area with houses, a marina, and a flag.

2. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
CA $284
CA $729 total
includes taxes & fees
Oct 9 - Oct 10
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.
A waterfront property with a boat dock, a covered outdoor seating area, and a two-story building with balconies.
A resort with a swimming pool, beach area, and marina.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

3. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
CA $560
CA $1,079 total
includes taxes & fees
Oct 9 - Oct 10
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A living room with a sofa, chairs, a coffee table, a TV, and large windows overlooking the ocean.
A covered outdoor seating area with turquoise Adirondack chairs and a small round table, overlooking a beach with palm trees and a pier.
A resort with a swimming pool, beach area, and marina.

4. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
CA $582
CA $1,197 total
includes taxes & fees
Oct 10 - Oct 11
Post Card Point #319 - Ocean Views!
View all properties

Choose what matters most at ski hotels in Key West

Resort
4 stars
5 stars
Spa
Family-friendly

Top Key West Hotel Reviews

Explore a world of travel with Expedia