Condo
10.0(220 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
Parking
Pool
Ocean View
Balcony/Terrace
CA $505/Night
7 Nights - CA $3,537
Key West Ski Chalets
10.0
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
Breakfast- Parking
- Pool
View
CA $1,335/Night
7 Nights - CA $9,348
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
Kitchen
CA $1,110/Night
7 Nights - CA $7,769
House
10.0(208 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $764/Night
7 Nights - CA $5,349
House
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- View
Pet Friendly
Child Friendly
Security/Safety
CA $510/Night
7 Nights - CA $3,569
Condo
10.0(194 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $527/Night
7 Nights - CA $3,690
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
Internet- Child Friendly
Laundry- Security/Safety
CA $3,490/Night
7 Nights - CA $24,433
House
10.0(193 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $1,092/Night
7 Nights - CA $7,642
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Parking
- Pool
- View
Air Conditioner
CA $1,876/Night
7 Nights - CA $13,130
House
10.0(189 Reviews)
2 Bedrooms
2 Baths
6 Guests
765 ft²
Private Pool- Pool
- Balcony/Terrace
- Kitchen
CA $1,200/Night
7 Nights - CA $8,397
Condo
10.0(178 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
Oceanfront- Parking
- Pool
- Ocean View
CA $276/Night
7 Nights - CA $1,933
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.
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
New Town
The Meadows
Meadows
Bahama Village
Midtown
Frequently Asked Questions About Key West Rental Ski Chalets
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:
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Perfect Location, Private Heated Pool, Pristine Luxury Home!
- Walkable Cottage w/Pool Access in Key West!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- ~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
- Secret Villa II @ Old Town: with Private Pool, close to Duval!
- *AMERICANA TROPICALE @ OLD TOWN* Home & Pool + Last Key White Glove Service.
2. How many Ski Chalets are available in Key West?
Currently, the total number of properties listed by RBO in 2026 is over 5125 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
House
10.0(3 Reviews)
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1 Bath
2 Guests
- Breakfast
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Condo
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Condo
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Condo
10.0(152 Reviews)
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House
10.0(141 Reviews)
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- Parking
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CA $2,027/Night
7 Nights - CA $14,190
House
10.0(139 Reviews)
2 Bedrooms
1 Bath
6 Guests
792 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $922/Night
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House
10.0(135 Reviews)
2 Bedrooms
2 Baths
4 Guests
840 ft²
- Hot Tub
- Parking
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CA $1,101/Night
7 Nights - CA $7,706
Condo
10.0(130 Reviews)
2 Bedrooms
2 Baths
6 Guests
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- Oceanfront
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Condo
10.0(126 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $361/Night
7 Nights - CA $2,524
Condo
10.0(121 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $437/Night
7 Nights - CA $3,060
