Key West Ski Chalets
New
House
10.0(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1564 ft²
Oceanfront
Parking
Pool
Ocean View
CA $926/Night
7 Nights - CA $6,482
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
Breakfast- Parking
- Pool
View
CA $1,337/Night
7 Nights - CA $9,361
Cottage
10.0(6 Reviews)
1 Bedroom
1 Bath
- Ocean View
Balcony/Terrace- View
Kitchen
CA $790/Night
7 Nights - CA $5,530
House
10.0(8 Reviews)
7 Bedrooms
8 Baths
16 Guests
Private Pool- Parking
- Pool
- Balcony/Terrace
CA $2,520/Night
7 Nights - CA $17,644
House
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
Pet Friendly
Child Friendly
Security/Safety
CA $511/Night
7 Nights - CA $3,574
New
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
8 Guests
1560 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $640/Night
7 Nights - CA $4,479
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
Internet- Child Friendly
Laundry- Security/Safety
CA $3,778/Night
7 Nights - CA $26,447
New
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1040 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $493/Night
7 Nights - CA $3,454
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Parking
- Pool
- View
Air Conditioner
CA $1,878/Night
7 Nights - CA $13,148
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
782 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $405/Night
7 Nights - CA $2,835
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Breakfast
- Parking
- Pool
- View
CA $1,250/Night
7 Nights - CA $8,748
House
9.8(131 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $607/Night
7 Nights - CA $4,252
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
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
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- 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
- 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
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
2. How many Ski Chalets are available in Key West?
Currently, the total number of properties listed by RBO in 2026 is over 4991 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
- Breakfast
- Parking
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House
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New
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10 Guests
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New
Cottage
9.6(16 Reviews)
1 Bedroom
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4 Guests
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Cottage
9.4(23 Reviews)
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- View
CA $897/Night
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Boat Rental
9.2(11 Reviews)
2 Bedrooms
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6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $483/Night
7 Nights - CA $3,379
House
8.4(5 Reviews)
2 Bedrooms
3 Baths
6 Guests
- Parking
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- Balcony/Terrace
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CA $844/Night
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New
Apartment
8.0(18 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $469/Night
7 Nights - CA $3,280
House
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $950/Night
7 Nights - CA $6,652
House
3 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $911/Night
7 Nights - CA $6,380
New
House
3 Bedrooms
2 Baths
6 Guests
703 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $361/Night
7 Nights - CA $2,524
