Best Vacation Homes in Upper Matecumbe Key
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Upper Matecumbe Key Luxury Rentals
- 3771 ft² House
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Upper Matecumbe Key Pet Friendly Vacation Rentals
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- 3999 ft² House
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Upper Matecumbe Key Large Vacation Homes
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- 667 ft² Villa
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Why Choose Rent By Owner for your Upper Matecumbe Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Upper Matecumbe Key Vacation Rentals
Where are the best neighborhoods to stay in Upper Matecumbe Key?
When choosing where to stay in Upper Matecumbe Key, Florida, you’ll find a variety of neighborhoods that offer a perfect blend of tranquility and accessibility. This area is renowned for its scenic waterfront views and peaceful atmosphere, making it an ideal location for those seeking a relaxing retreat. Whether you prefer staying closer to the calm waters or within a short drive to local amenities, there are neighborhoods that cater to different preferences. By selecting your vacation rental in this charming part of the Florida Keys, you'll enjoy the natural beauty and laid-back vibe that define Upper Matecumbe Key.
Coral Cove
Stay in Coral Cove, where the peaceful surroundings and natural beauty offer an ideal setting for relaxing by the water. This area provides easy access to the scenic coastline, making it perfect for those seeking a tranquil retreat in the region.
View 542+ Rentals in Coral CoveBest Times to Visit Upper Matecumbe Key
When should you plan your Vacation Rentals stay?
Choosing the best time to visit this destination can greatly enhance your experience, so consider planning your trip during the region’s optimal seasons for ideal weather and fewer crowds.
Peak Season Highlights
Spring (March to May)
During spring, the region experiences warm and inviting weather, making it ideal for outdoor activities and exploring the area’s natural beauty.
Winter (December to February)
The winter months bring mild temperatures and less rainfall, offering a perfect escape from colder climates while enjoying sunny days here.
Off-Season Highlights
Summer (June to August)
Mid-summer sees hotter and more humid conditions, with occasional rain showers, but it remains a popular time for those seeking lively coastal adventures.
Fall (September to November)
As the region transitions into fall, the weather cools slightly, and fewer visitors mean more tranquil surroundings for your stay.
Weekly Weather Forecast for Upper Matecumbe Key
How to Book Your Upper Matecumbe Key Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Upper Matecumbe Key
Common Vacation Rentals Amenities
What amenities can you expect?
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
- Private outdoor pools for relaxing and swimming in the warm Florida sun.
- Spacious patios or decks ideal for outdoor dining and entertaining.
- Well-maintained barbecue grills to enjoy grilled meals with friends and family.
- Direct access to scenic waterfronts or beaches perfect for sunbathing and water activities.
- Outdoor showers for rinsing off after a day at the beach or exploring the region.
- Comfortable lounge chairs or hammocks to unwind while soaking up the tropical atmosphere.
- Expansive yards or gardens providing space for outdoor games and leisure activities.
Top Attractions Around Upper Matecumbe Key
What attractions are nearby?
Enjoy a variety of outdoor activities such as kayaking, snorkeling, and fishing just steps from your vacation rental in this scenic area, offering the perfect opportunity to explore the stunning natural beauty of the region.
Family Activities
- Snorkeling Adventures: Explore the vibrant coral reefs and marine life just off the coast, offering an engaging outdoor activity for families seeking fun in the water.
- Key Largo Undersea Park: Discover a fascinating underwater park that provides educational tours and snorkeling opportunities, perfect for family outings in this scenic area.
- Fishing Charters: Embark on a family-friendly fishing trip where you can experience the region's rich aquatic environment firsthand and create memorable moments together.
- Kayaking Tours: Enjoy serene paddling experiences along calm waters, providing an excellent way for families to connect with nature in this coastal destination.
Adult Activities
- Snorkeling and Diving: Explore vibrant coral reefs and marine life just off the coast, making it a perfect activity for underwater enthusiasts staying in this destination.
- Fishing Excursions: Enjoy guided fishing trips in the region’s abundant waters, ideal for anglers looking to experience local fishing spots from your vacation rental base.
- Kayaking and Paddleboarding: Glide across calm waters and discover hidden coves along the shoreline, offering a peaceful retreat for water sport lovers here.
- Sunset Cruises: Embark on a scenic boat tour in the area to witness breathtaking sunsets, creating memorable moments during your stay in the region.
Other Places to Stay in Upper Matecumbe Key, FL
Upper Matecumbe Key Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Water Activities: Make the most of your stay by indulging in kayaking or paddleboarding along the serene waters that surround this destination, offering an authentic experience of the area's natural beauty.
- Visit Nearby Marine Spots: Take advantage of the region’s vibrant marine life by booking a snorkeling tour or a fishing trip to enjoy the underwater wonders just off the coast.
- Select a Prime Location: When choosing your vacation rental, prioritize properties close to popular beaches and waterways to conveniently access the area’s scenic attractions and activities.
- Plan for Local Dining Experiences: Savor the flavors of the region by exploring nearby waterfront restaurants and eateries that showcase fresh, local seafood specialties.
Transportation Options
- Car Rentals: Renting a vehicle is an ideal way to explore the scenic views and hidden spots around this destination at your own pace.
- Local Taxis and Rideshare Services: Taxis and rideshare options provide convenient, on-demand transportation for quick trips across the area.
- Bike Rentals: Biking offers a scenic and eco-friendly way to discover the region's natural beauty while enjoying the fresh sea breeze.
- Public Transportation: Limited but reliable bus services connect key points here, making it a practical option for budget-conscious travelers.
Local Customs Options
- Respect for Marine Life: Locals here emphasize preserving the vibrant marine ecosystem, encouraging visitors to avoid disturbing coral reefs and wildlife during their stay.
- Conservation of Natural Resources: It is customary to practice eco-friendly habits, such as recycling and conserving water, to protect the region’s delicate environment.
- Celebration of Local Art and Craftsmanship: Engaging with community art shows and craft markets highlights the area's rich cultural heritage and appreciation for handmade works.
- Gulf Coast Hospitality: Visitors are often greeted with warm friendliness and a laid-back attitude that reflects the region's welcoming coastal traditions.
Frequently Asked Questions About Upper Matecumbe Key?
What are the top vacation rentals 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 Vacation Rentals in Upper Matecumbe Key:
- OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
- OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
- The Caribbean Resort
- AQUAMARINE OCEANVIEW “FLASH SALE”JUNE/JULY+ DOCK+POOL+GYM+”150” 5 STAR REVIEWS
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
How many vacation rentals have private pools in Upper Matecumbe Key?
There are 204 vacation rentals with private pools near Upper Matecumbe Key. Top-rated RBO homes that have access to a swimming pool include:
Which vacation homes in Upper Matecumbe Key are best for families?
If you are looking for a family-friendly vacation home in Upper Matecumbe Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upper Matecumbe Key:
How many Rentbyowner vacation rentals are available in Upper Matecumbe Key?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1358 in the Upper Matecumbe Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Upper Matecumbe Key.
Upper Matecumbe Key Top Rated Vacation Rentals
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