Longboat Key Ski Chalets
New
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1072 ft²
Fireplace/Heating
Pool
Balcony/Terrace
Kitchen
US $267/Night
7 Nights - US $1,871
Apartment
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
1259.38 ft²
Private Pool
Private Beach
Oceanfront- Fireplace/Heating
US $283/Night
7 Nights - US $1,981
US $1,134/Night
7 Nights - US $7,938
Condo
2 Bedrooms
2 Baths
6 Guests
1623 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Pool
US $226/Night
7 Nights - US $1,582
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
333.68 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $437/Night
7 Nights - US $3,057
New
Condo
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
Spa- Pool
US $154/Night
7 Nights - US $1,079
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
6 Guests
699.65 ft²
- Private Beach
- Oceanfront
- Pool
Ocean View
US $418/Night
7 Nights - US $2,926
Condo
10.0(208 Reviews)
1 Bedroom
1 Bath
6 Guests
800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $493/Night
7 Nights - US $3,451
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1743.75 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $957/Night
7 Nights - US $6,699
Condo
10.0(134 Reviews)
1 Bedroom
1 Bath
6 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $609/Night
7 Nights - US $4,265
Apartment
10.0(1 Review)
21 Bedrooms
2 Baths
4 Guests
1194.79 ft²
- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
US $411/Night
7 Nights - US $2,877
Condo
10.0(68 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $585/Night
7 Nights - US $4,097
Why Choose Rent By Owner for your Longboat 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 Longboat Key
How to Book Your Longboat 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 Longboat 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
Other Places to Stay in Longboat Key, FL
Jewfish Key
Beer Can Island
Longbeach Village
Quick Point Nature Reserve
Cannons Marina
Harborside Golf Course at Longboat Key Club
Islandside Golf Course at Longboat Key Club
Bay Isles
Longboat Key Beaches
Longboat Key Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets in Longboat Key?
There are a lot of options in Longboat Key. If you plan on staying in the Longboat 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 Longboat Key:
- Longboat Key Waterfront 3BR house w/Pool in most desirable Country Club Shores
- UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY
- 3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!
- Gorgeous Gulf views and a beachfront location!
- Longboat Key home on the canal and a 5 minute walk to the beach
- Beautiful pool home in the historic village of Longboat Key | Close to beach - Longboat Oasis
- Beachfront Longboat Key Condo 3BR Pool, Tennis & Private Beach Access
- Exquisite 3 BR/3.5 BA home with pool and spa on Longboat Key - The Captain's Quarters
- Fantastic Beach Condo
- Longboat Key near St Armands Beachside Sanctuary 2BR/2BA w/Full Kitchen
2. How many Ski Chalets are available in Longboat Key?
Currently, the total number of properties listed by RBO in 2026 is over 848 in the Longboat Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Longboat Key.
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Apartment
9.8(8 Reviews)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Oceanfront
- Spa
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US $312/Night
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Condo
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4 Guests
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Condo
10.0(11 Reviews)
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Condo
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Condo
10.0(8 Reviews)
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6 Guests
- Fireplace/Heating
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Condo
10.0(6 Reviews)
2 Bedrooms
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Condo
10.0(6 Reviews)
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Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1172 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $256/Night
7 Nights - US $1,795
Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $175/Night
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Condo
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $432/Night
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