Key West Ski Chalets
1222 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,424/Night
For 7 Nights US $9,970
2002.09 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Breakfast
- Parking
US $953/Night
For 7 Nights US $6,673
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Pool
- Ocean View
- Balcony/Terrace
US $462/Night
For 7 Nights US $3,234
1618 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,451/Night
For 7 Nights US $10,155
1496.18 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Breakfast
- Parking
US $891/Night
For 7 Nights US $6,236
1750 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,132/Night
For 7 Nights US $7,924
6 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
Apartment
- View
- Pet Friendly
- Parking
US $467/Night
For 7 Nights US $3,267
3500 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $999/Night
For 7 Nights US $6,993
2895.49 ft²
14 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- View
US $2,969/Night
For 7 Nights US $20,783
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $956/Night
For 7 Nights US $6,694
796.53 ft²
8 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pool
- View
US $1,658/Night
For 7 Nights US $11,606
3000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $622/Night
For 7 Nights US $4,357
Why Choose Rent By Owner for your Key West Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Key West
How to Book Your Key West Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Key West
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Key West, FL
Key West Historic District
Old Town
Duval Street
Downtown
Uptown - Upper Duval
Historic Seaport
Truman Annex
The Meadows
Meadows
New Town
Bahama Village
Midtown
Key West Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets in Key West?
There are a lot of options in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Key West:
- Almond Tree Inn Hotel - Adults Only
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
2. How many Ski Chalets are available in Key West?
Currently, the total number of properties listed by RBO in 2026 is over 4879 in the Key West area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Key West.
More Rentals You May Like Near Key West
398.26 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Pool
- View
US $609/Night
For 7 Nights US $4,263
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Boat Rental
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $489/Night
For 7 Nights US $3,422
6 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $432/Night
For 7 Nights US $3,021
650 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $382/Night
For 7 Nights US $2,677
1588 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $382/Night
For 7 Nights US $2,675
1350 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- Kitchen
- Air Conditioner
US $349/Night
For 7 Nights US $2,446
1747 ft²
6 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $335/Night
For 7 Nights US $2,342
1060 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Pet Friendly
US $276/Night
For 7 Nights US $1,934
1533 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Pet Friendly
US $252/Night
For 7 Nights US $1,762
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $212/Night
For 7 Nights US $1,485
622 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $183/Night
For 7 Nights US $1,281
405 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $181/Night
For 7 Nights US $1,266
