Upper Harbor Key Ski Chalets
New
House
10.0(8 Reviews)
4 Bedrooms
2 Baths
8 Guests
2300 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
CA $542/Night
7 Nights - CA $3,793
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
861.11 ft²
Oceanfront
Hot Tub
Spa
Pool
CA $670/Night
7 Nights - CA $4,688
House
10.0(1 Review)
1 Bedroom
1 Bath
- Balcony/Terrace
Pet Friendly- Parking
Internet
CA $1,027/Night
7 Nights - CA $7,192
House
9.8(12 Reviews)
3 Bedrooms
3 Baths
10 Guests
Private Pool- Fireplace/Heating
- Pool
Ocean View
CA $720/Night
7 Nights - CA $5,039
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Hot Tub
- Spa
- Pool
- Pet Friendly
CA $600/Night
7 Nights - CA $4,199
New
House
9.4(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
1794 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $600/Night
7 Nights - CA $4,197
House
9.6(2 Reviews)
5 Bedrooms
4 Baths
10 Guests
2228.13 ft²
- Pet Friendly
- Parking
Air Conditioner- Internet
CA $430/Night
7 Nights - CA $3,009
House
8.4(12 Reviews)
3 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $1,012/Night
7 Nights - CA $7,082
House
9.4(6 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Pet Friendly
- Parking
- Internet
Child Friendly
CA $438/Night
7 Nights - CA $3,068
New
House
8.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2952 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,243/Night
7 Nights - CA $8,700
House
9.2(21 Reviews)
2 Bedrooms
2 Baths
5 Guests
861.11 ft²
Private Beach- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $474/Night
7 Nights - CA $3,321
House
2 Bedrooms
2 Baths
6 Guests
960 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $205/Night
7 Nights - CA $1,434
Why Choose Rent By Owner for your Upper Harbor Key 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 Upper Harbor Key
How to Book Your Upper Harbor Key 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 Upper Harbor Key
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
Frequently Asked Questions About Upper Harbor Key Rental Ski Chalets
1. What are the top Ski Chalets in Upper Harbor Key?
There are a lot of options in Upper Harbor Key. If you plan on staying in the Upper Harbor Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Upper Harbor Key:
- Yellow Home - Receive 400 dollars towards a BOAT RENTAL!
- Waterfront Beach Houses with Dock & Heated Pool!
- Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
- Starfish - Ocean front with dock and pool
- Looking for a place to stay?
- A Tropical Luxury Getaway, Your own private resort!
- Conch House - Ocean front with dock and pool
2. How many Ski Chalets are available in Upper Harbor Key?
Currently, the total number of properties listed by RBO in 2026 is over 1225 in the Upper Harbor Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Upper Harbor Key.
More Rentals You May Like Near Upper Harbor Key
Villa
9.2(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Pool
CA $1,284/Night
7 Nights - CA $8,986
House
10.0(240 Reviews)
2 Bedrooms
3 Baths
6 Guests
1200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $861/Night
7 Nights - CA $6,027
House
10.0(213 Reviews)
2 Bedrooms
3 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $692/Night
7 Nights - CA $4,848
Cottage
10.0(67 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
CA $804/Night
7 Nights - CA $5,630
House
10.0(52 Reviews)
2 Bedrooms
2 Baths
6 Guests
1296 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $699/Night
7 Nights - CA $4,893
House
10.0(47 Reviews)
2 Bedrooms
2 Baths
6 Guests
864 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $628/Night
7 Nights - CA $4,394
Cottage
10.0(45 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
CA $402/Night
7 Nights - CA $2,812
House
10.0(40 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $998/Night
7 Nights - CA $6,987
House
10.0(37 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $522/Night
7 Nights - CA $3,657
Villa
10.0(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $848/Night
7 Nights - CA $5,939
House
10.0(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
1152 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $385/Night
7 Nights - CA $2,696
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $817/Night
7 Nights - CA $5,716
