Key West Ski Chalets
House
10.0(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
1564 ft²
Oceanfront
Pool
Ocean View
Balcony/Terrace
AU $1,041/Night
7 Nights - AU $7,285
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Pool
View
Breakfast
Parking
AU $1,370/Night
7 Nights - AU $9,593
Cottage
10.0(6 Reviews)
1 Bedroom
1 Bath
- Ocean View
- Balcony/Terrace
- View
Pet Friendly
AU $810/Night
7 Nights - AU $5,667
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
782 ft²
- Pool
- Balcony/Terrace
Kitchen- Parking
AU $244/Night
7 Nights - AU $1,705
House
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Pet Friendly
Child Friendly
Security/Safety
AU $523/Night
7 Nights - AU $3,663
House
9.8(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
Private Pool- Oceanfront
- Pool
- Ocean View
AU $765/Night
7 Nights - AU $5,356
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
Internet- Child Friendly
Laundry- Security/Safety
AU $3,872/Night
7 Nights - AU $27,103
Cottage
9.4(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
AU $919/Night
7 Nights - AU $6,436
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
Fireplace/Heating- Pool
- View
- Pet Friendly
AU $1,925/Night
7 Nights - AU $13,474
New
Apartment
8.0(18 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
AU $461/Night
7 Nights - AU $3,230
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Pool
- View
- Breakfast
- Parking
AU $1,281/Night
7 Nights - AU $8,965
House
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $974/Night
7 Nights - AU $6,817
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
Midtown
Key West Historic District
Old Town
Duval Street
Downtown
Uptown - Upper Duval
Historic Seaport
Truman Annex
The Meadows
Meadows
New Town
Bahama Village
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:
- Almond Tree Inn Hotel - Adults Only
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Everything Key West has to offer @ Mango Cottage
- Secret Villa I @ Old Town with Private Pool, close to Duval!
- Key West Rooster
- Your Condo by the Beach with Ocean View
- Secret Villa II @ Old Town: with Private Pool, close to Duval!
2. How many Ski Chalets are available in Key West?
Currently, the total number of properties listed by RBO in 2026 is over 5027 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)
1 Bedroom
1 Bath
2 Guests
- Pool
- View
- Breakfast
- Parking
AU $363/Night
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House
3 Bedrooms
2 Baths
8 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
AU $878/Night
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New
House
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2 Baths
10 Guests
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- Fireplace/Heating
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House
2 Bedrooms
2 Baths
5 Guests
650 ft²
- Oceanfront
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- View
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New
Hotel
10.0(2 Reviews)
3 Baths
- Fireplace/Heating
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10.0(2 Reviews)
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New
Hotel
10.0(2 Reviews)
2 Baths
- Fireplace/Heating
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New
Hotel
10.0(1 Review)
6 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
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Hotel
10.0(1 Review)
4 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $1,616/Night
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New
Hotel
9.2(5 Reviews)
3 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $1,055/Night
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New
Hotel
9.0(4 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $481/Night
7 Nights - AU $3,370
Hotel
7.0(2 Reviews)
6 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $2,109/Night
7 Nights - AU $14,761
