1. USA
  2. Florida
  3. Islamorada
  4. Ski Chalets

Islamorada Ski Chalets

New
4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pet Friendly
  • Kitchen
AU $396/Night For 7 Nights AU $2,775
10.0
Exceptional
(2 Reviews)
1679.17 ft² 6 Guests 3 Bedrooms 3 Bathrooms
House
  • Spa
  • Pool
  • View
AU $1,367/Night For 7 Nights AU $9,570
9.8
Exceptional
(72 Reviews)
4 Guests 1 Bedroom 1 Bathroom
Ocean View Villa
  • Oceanfront
  • Hot Tub
  • Spa
AU $1,350/Night For 7 Nights AU $9,451
New
4 Guests 1 Bedroom 1 Bathroom
Ocean View Condo
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $231/Night For 7 Nights AU $1,615
10.0
Exceptional
(1 Review)
10.76 ft² 10 Guests 1 Bedroom 5 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $3,538/Night For 7 Nights AU $24,766
10.0
Exceptional
(191 Reviews)
6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $724/Night For 7 Nights AU $5,068
9.6
Exceptional
(19 Reviews)
1550 ft² 6 Guests 2 Bedrooms 2 Bathrooms
House
  • Private Beach
  • Oceanfront
  • Fireplace/Heating
AU $566/Night For 7 Nights AU $3,963
10.0
Exceptional
(185 Reviews)
1200 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $714/Night For 7 Nights AU $5,000
9.5
Exceptional
(9 Reviews)
1001.04 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Apartment
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $268/Night For 7 Nights AU $1,874
10.0
Exceptional
(170 Reviews)
1386 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $706/Night For 7 Nights AU $4,945
9.5
Exceptional
(4 Reviews)
527.43 ft² 5 Guests 2 Bedrooms 1 Bathroom
House
  • Oceanfront
  • Pool
  • Ocean View
AU $436/Night For 7 Nights AU $3,051
10.0
Exceptional
(157 Reviews)
1700 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View Condo
  • Oceanfront
  • Hot Tub
  • Fireplace/Heating
AU $630/Night For 7 Nights AU $4,407

Why Choose Rent By Owner for your Islamorada Ski Chalets?

What makes our Ski Chalets special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Islamorada

When should you plan your Ski Chalets stay?

To make the most of your visit here, consider planning your vacation during the region's ideal seasons when the weather complements outdoor activities and ensures a comfortable stay in your chosen ski chalets.

Peak Season Highlights

winter
Winter (December to February)

During these months, the region experiences its peak tourist influx, making it an ideal time for you to enjoy the vibrant atmosphere and warm weather escapes in this destination.

Average Temperature Daytime: 76°F - Nighttime: 65°F
spring
Spring Break (March to April)

This period sees a surge of visitors seeking a lively environment and sunny days, perfect for exploring and relaxing in your chosen property here in the region.

Average Temperature Daytime: 78°F - Nighttime: 67°F

Off-Season Highlights

image
Summer (June to August)

The off-peak summer months tend to be quieter, offering you a more tranquil experience while enjoying warm temperatures and less crowded beaches.

Average Temperature Daytime: 88°F - Nighttime: 74°F
image
Fall (September to November)

During fall, the area becomes less busy, providing a peaceful retreat and ideal conditions for relaxation and outdoor activities in a serene setting.

Average Temperature Daytime: 82°F - Nighttime: 69°F

Weekly Weather Forecast for Islamorada

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.

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

Outdoor Amenities

  • Enjoy access to private or shared outdoor pools with scenic views of the surrounding waters.
  • Relax on spacious, furnished decks ideal for soaking up the sunshine and ocean breezes.
  • Take advantage of direct access to pristine beaches for swimming, sunbathing, or beachcombing.
  • Utilize outdoor grilling areas perfect for hosting barbecues with family and friends.
  • Explore well-maintained walking paths and serene gardens nearby for leisure strolls.
  • Benefit from outdoor dining spaces that allow you to enjoy meals with a view.
  • Make use of boat docks or slips if you plan to explore the region by watercraft.
image
image

Family Activities

  • Everglades National Park Tour Embark on a family-friendly airboat tour to explore the unique and diverse ecosystem of the nearby Everglades, providing an exciting adventure for all ages.
  • John Pennekamp Coral Reef State Park Spend a day snorkeling or glass-bottom boating in this renowned park, where your family can discover colorful coral reefs and marine life just off the coast.
  • Florida Keys Wild Bird Rehabilitation Center Visit this educational center to learn about local bird species and conservation efforts, offering a meaningful experience for nature-loving families.
  • Fishing Charters Enjoy a family fishing excursion with expert guides who will take you to prime spots, making it a memorable outdoor activity in the region.
image

Adult Activities

  • Fishing Charters: Embark on a local fishing charter to experience some of the best sportfishing adventures in the region, perfect for anglers seeking a thrilling day on the water.
  • Water Sports and Snorkeling: Explore the vibrant underwater world through snorkeling or paddleboarding, allowing you to enjoy the clear waters and diverse marine life that this destination is known for.
  • Wildlife Viewing and Eco-Tours: Discover the area's natural beauty by taking wildlife tours that showcase the region’s unique ecosystems and abundant birdlife.
  • Dining Experiences: Savor fresh seafood and local cuisine at renowned restaurants, making every meal an integral part of your memorable visit here.

Other Places to Stay in Islamorada, FL

History of Diving Museum
Seabreeze Trailer Park
Windley Key Fossil Reef Geological State Park
Theater of the Sea
Matecumbe United Methodist Church
Upper Matecumbe Key
Plantation by the Sea
White Marlin Beach
Lower Matecumbe Beach
Toll Gate Shores
Venetian Shores

Islamorada Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: To maximize your stay, explore the region’s popular water-based activities and secure bookings early for a smooth experience.
  • Opt for Waterfront Properties: Choosing a ski chalet with direct access to the water can elevate your visit, offering picturesque views and easy engagement with the area's natural beauty.
  • Discover Local Dining and Culture: Take time to sample local cuisine and participate in cultural experiences that showcase the unique charm of this destination.
  • Utilize Guided Tours and Excursions: Enhance your stay by booking guided tours to explore hidden gems and enjoy expert insights about the region's marine life and environment.

Transportation Options

  • Car Rentals Renting a car in Islamorada allows you to explore the region at your own pace and access remote beaches or fishing spots easily.
  • Public Transportation The local bus services provide a budget-friendly way to navigate the area and reach key attractions without hassle.
  • Taxis and Rideshare Services Taxis and rideshare options like Uber or Lyft offer convenient, on-demand transportation for quick trips around here.
  • Bike Rentals For a more eco-friendly and leisurely experience, bike rentals are available, enabling you to enjoy scenic views at your own pace.

Local Customs Options

  • Respect for Local Religious Practices: Visitors are encouraged to observe and honor the Islamic customs practiced here, including respectful attire and behavior during visits to mosques or religious sites.
  • Greetings and Social Etiquette: It’s customary to greet locals with a polite "As-Salaamu Alaikum," reflecting the region’s Islamic cultural influence and fostering respectful interactions.
  • Dietary Restrictions: Many residents and establishments adhere to halal dietary laws, so being mindful of this when dining or shopping helps demonstrate appreciation for local traditions.
  • Community Events and Celebrations: Participating in or observing Islamic festivals and community gatherings offers insight into the area's spiritual heritage and social customs.

Frequently Asked Questions About Islamorada Rental Ski Chalets

2. How many Ski Chalets are available in Islamorada?

Currently, the total number of properties listed by RBO in 2026 is over 1540 in the Islamorada area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Islamorada. 

3. What is the cancellation policy for booking a ski chalet in this area?

The cancellation policy varies depending on the specific property you choose. You should review the individual listing details or contact the owner directly for exact information regarding cancellations and potential fees.

4. Are there any additional fees or deposits required when staying at a ski chalet here?

Additional fees such as cleaning charges, security deposits, or service fees may apply. Details are typically provided in the listing description, so it’s recommended to review these before confirming your booking or reaching out to the owner for clarification.

5. What amenities can I expect during my stay at a ski chalet in this destination?

Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. For specific features available, be sure to check the property listing or contact the owner directly.

6. Is early check-in or late check-out available at ski chalets here?

Availability of early check-in or late check-out depends on the individual property’s schedule and policies. You should inquire directly with the host when making your reservation to see if these options can be accommodated.

7. How do I ensure my booking is secure and reliable in this region?

Bookings are generally protected through secure payment systems and verified listings. To ensure a seamless experience, always review the host’s reviews and confirm details directly through the booking platform or the property owner.

More Rentals You May Like Near Islamorada

9.5
Exceptional
(2 Reviews)
1302.43 ft² 6 Guests 2 Bedrooms 3 Bathrooms
Villa
  • Private Beach
  • Oceanfront
  • Pool
AU $701/Night For 7 Nights AU $4,904
10.0
Exceptional
(144 Reviews)
6 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $478/Night For 7 Nights AU $3,348
10.0
Exceptional
(135 Reviews)
1100 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Cottage
  • Ocean View
  • Balcony/Terrace
  • View
AU $443/Night For 7 Nights AU $3,098
10.0
Exceptional
(118 Reviews)
1380 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View Villa
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $556/Night For 7 Nights AU $3,893
10.0
Exceptional
(113 Reviews)
4 Guests 1 Bedroom 1 Bathroom
Ocean View Cottage
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
AU $381/Night For 7 Nights AU $2,669
10.0
Exceptional
(106 Reviews)
1550 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
AU $548/Night For 7 Nights AU $3,835
10.0
Exceptional
(100 Reviews)
2000 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
AU $658/Night For 7 Nights AU $4,602
10.0
Exceptional
(99 Reviews)
1700 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Fireplace/Heating
  • Pool
  • Ocean View
AU $987/Night For 7 Nights AU $6,911
10.0
Exceptional
(98 Reviews)
5 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Oceanfront
  • Hot Tub
  • Fireplace/Heating
AU $935/Night For 7 Nights AU $6,545
10.0
Exceptional
(95 Reviews)
1700 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $909/Night For 7 Nights AU $6,360
10.0
Exceptional
(93 Reviews)
980 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View Villa
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
AU $507/Night For 7 Nights AU $3,551
10.0
Exceptional
(90 Reviews)
1300 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
AU $630/Night For 7 Nights AU $4,410