Upper Matecumbe Key Ski Chalets
House
10.0(77 Reviews)
5 Bedrooms
6 Baths
10 Guests
4000 ft²
Private Pool
Hot Tub
Fireplace/Heating
Pool
CA $3,428/Night
7 Nights - CA $23,994
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1679.17 ft²
Spa- Pool
View
Breakfast
CA $1,373/Night
7 Nights - CA $9,608
House
9.6(256 Reviews)
1 Bedroom
1 Bath
- Pool
Ocean View
Balcony/Terrace- View
CA $385/Night
7 Nights - CA $2,694
New
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $529/Night
7 Nights - CA $3,704
House
10.0(1 Review)
1 Bedroom
5 Baths
10 Guests
10.76 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $3,552/Night
7 Nights - CA $24,865
House
9.0(4 Reviews)
2 Bedrooms
2 Baths
9 Guests
1428 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $273/Night
7 Nights - CA $1,910
Apartment
9.5(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $269/Night
7 Nights - CA $1,881
Apartment
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $385/Night
7 Nights - CA $2,697
House
9.5(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
527.43 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $438/Night
7 Nights - CA $3,063
Hotel
10.0(2 Reviews)
2 Baths
676 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
CA $1,257/Night
7 Nights - CA $8,798
House
9.5(2 Reviews)
3 Bedrooms
3 Baths
7 Guests
1700.7 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,086/Night
7 Nights - CA $7,599
New
Hotel
10.0(2 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
Kitchen
CA $571/Night
7 Nights - CA $3,994
Why Choose Rent By Owner for your Upper Matecumbe 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.
Popular Areas for Upper Matecumbe Key Ski Chalets
Where are the best neighborhoods to stay in Upper Matecumbe Key?
Discover the charming neighborhoods of Upper Matecumbe Key, Florida, where you can enjoy a serene and picturesque setting perfect for your stay. This area offers a variety of accommodations that provide both comfort and accessibility to local attractions. Whether you're seeking a peaceful retreat or a convenient base for exploring the region, staying in these neighborhoods ensures a reliable and enjoyable experience for your visit.
Coral Cove
In this part of the region, you will find a peaceful atmosphere ideal for relaxing stays. The area offers convenient access to the natural beauty of nearby beaches and waterfront scenery, perfect for enjoying your time in Florida.
View 643+ Rentals in Coral CoveBest Times to Visit Upper Matecumbe Key
When should you plan your Ski Chalets stay?
To make the most of your stay in this destination, consider planning your visit during the optimal seasons when pleasant weather enhances your experience and outdoor activities are at their best, making it an ideal time to book your ski chalets here through RentByOwner.com for a seamless and reliable vacation experience.
Peak Season Highlights
Winter (December to February)
During the winter months, you can experience the warm climate of this destination, making it an ideal time for exploring and enjoying outdoor activities.
Average Temperature Daytime: around 75°F - Nighttime: mid 60s°F
Spring Break (March to April)
This is when the area sees a surge in visitors seeking pleasant weather and vibrant local events, perfect for a lively getaway.
Average Temperature Daytime: mid 70s°F to 80°F - Nighttime: low 70s°F
Off-Season Highlights
Summer (June to August)
The summer months tend to be quieter, offering tranquil surroundings and fewer tourists, ideal for those seeking relaxation away from crowds.
Average Temperature Daytime: high 80s°F to low 90s°F - Nighttime: mid 70s°F
Fall (September to November)
During fall, the region experiences fewer visitors, providing a peaceful environment for exploring and unwinding at your own pace.
Average Temperature Daytime: mid 70s°F - Nighttime: mid 60s°F
Weekly Weather Forecast for Upper Matecumbe Key
How to Book Your Upper Matecumbe 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 Matecumbe 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
Outdoor Amenities
- Enjoy private waterfront access for scenic views and water activities.
- Relax by the outdoor swimming pool with tropical surroundings.
- Utilize grilling stations for outdoor dining in a tropical setting.
- Take advantage of shaded patios or verandas perfect for lounging outdoors.
- Explore nearby walking or biking trails within the region’s natural beauty.
- Benefit from secure, covered parking to protect your vehicle during your stay.
- Make use of outdoor shower facilities to rinse off after beach or water excursions.
Top Attractions Around Upper Matecumbe Key
What attractions are nearby?
Within the region, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic nature trails, all conveniently accessible from your nearby Upper Matecumbe Key accommodation, offering an ideal setting to experience the natural beauty and tranquil surroundings that make this destination perfect for relaxing stays in cozy ski chalets.
Family Activities
- Snorkeling and Marine Exploration: Discover vibrant coral reefs and colorful marine life just off the coast, offering an engaging family activity in this coastal area.
- Wildlife Viewing Tours: Embark on guided tours to observe native bird species and other local wildlife thriving in the natural habitats here.
- Visit Local Parks and Beaches: Spend quality time relaxing and playing at family-friendly parks or pristine beaches that are perfect for sunbathing and picnicking.
- Kayaking Adventures: Enjoy safe and scenic kayaking excursions suitable for all ages, providing a fun way to explore the calm waters surrounding this destination.
Adult Activities
- Deep-sea Fishing: Embark on a guided deep-sea fishing trip to experience the region's abundant marine life and enjoy a day out on the water.
- Snorkeling Excursions: Explore the vibrant coral reefs and clear waters, discovering diverse sea creatures just off the coast of this island paradise.
- Kayaking Adventures: Paddle through calm, scenic waterways to observe local wildlife and enjoy tranquil surroundings unique to this destination.
- Sunset Cruises: Unwind on a boat cruise during sunset to take in breathtaking views and capture memorable moments in the region’s picturesque setting.
Other Places to Stay in Upper Matecumbe Key, FL
History of Diving Museum
Matecumbe United Methodist Church
Florida Keys Brewing Co.
Hurricane Monument
Coral Cove
Bud n' Mary's Dive Center
Islamorada
Upper Matecumbe Key Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Water Activities: Take advantage of the area's pristine waters by engaging in kayaking or snorkeling to fully experience the natural beauty surrounding your stay.
- Plan Your Outdoor Excursions: Schedule boat trips or nature walks during your visit to enjoy the scenic landscapes and diverse wildlife unique to this destination.
- Choose Convenient Accommodation Locations: Select a suitable ski chalet centrally located for easy access to both relaxation spots and outdoor adventures in the region.
- Prioritize Comfort and Amenities: Look for properties that offer modern conveniences like full kitchens and spacious living areas to enhance your comfort during your stay.
Transportation Options
- Rental Car Services: Car rental agencies in the region offer flexible transportation options to explore the scenic island and nearby attractions with ease.
- Public Transportation: Local bus services provide an affordable and convenient way to navigate the area without the need for a personal vehicle.
- Taxi and Rideshare Services: Taxis and rideshare platforms are readily available, offering quick and reliable transportation across this destination.
- Bicycle Rentals: Biking is a popular way to enjoy the natural beauty here, with numerous rental shops providing bikes suitable for all levels.
Local Customs Options
- Respect for Local Marine Life: Visitors are encouraged to observe marine wildlife respectfully, as the area is renowned for its vibrant coral reefs and diverse aquatic species.
- Quiet Hours and Low-Impact Living: The community values quiet evenings and environmentally conscious behavior to maintain the region’s tranquil atmosphere and pristine natural environment.
- Preservation of Cultural Heritage: Engaging with local traditions and supporting conservation efforts help preserve the area's unique history and cultural identity.
- Celebration of Local Festivals: Participating in regional festivals offers an authentic experience of the area's heritage and customs, enriching your stay here.
Frequently Asked Questions About Upper Matecumbe Key Rental Ski Chalets
1. What are the top Ski Chalets in Upper Matecumbe Key?
There are a lot of options in Upper Matecumbe Key. If you plan on staying in the Upper Matecumbe 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 Matecumbe Key:
- OCEANSIDE ANGLERS REEF 2/2.5 HOME- Gated community- Pool, Dock, Private Beach
- The Caribbean Resort
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
- Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach, plus Den
- Truly OceanFRONT-BestPanoramicOceanViews-VLgDecks-QuietestLocation-AvailableSlip
- Now booking heavily for 2027! - Oceanfront - Heated Pool - Dock
- Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
2. How many Ski Chalets are available in Upper Matecumbe Key?
Currently, the total number of properties listed by RBO in 2026 is over 1445 in the Upper Matecumbe 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 Matecumbe Key.
3. What is the cancellation policy for booking a ski chalet in this region?
Cancellation policies vary by listing. You should review the specific property's cancellation terms directly on its listing page or contact the owner for detailed information.
4. Are there any special requirements or restrictions when booking a ski chalet here?
Restrictions and requirements differ between properties. It's recommended to read the individual listing details carefully or reach out to the owner for specific policies regarding minimum stay, age limits, or other conditions.
5. How do I find available dates and secure my booking for a ski chalet in this area?
Available dates are displayed on each property’s listing. To reserve, follow the booking process outlined on the listing page or contact the owner for assistance.
6. Is there parking available at the ski chalets, and are there any fees involved?
Parking options and fees vary depending on the property. You should check the specific listing details or inquire directly with the owner to confirm parking arrangements.
7. What amenities can I expect during my stay in a ski chalet in the region?
Amenities differ from one property to another. Review each listing carefully to understand what is included, or contact the host directly for more information about the available facilities.
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