Best Vacation Homes in Upper Matecumbe Key
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $349/Night
For 7 Nights US $2,441
1679.17 ft²
6 Guests
3 Bedrooms
3 Bathrooms
House
- Spa
- Pool
- View
US $966/Night
For 7 Nights US $6,762
US $954/Night
For 7 Nights US $6,678
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $159/Night
For 7 Nights US $1,115
10.76 ft²
10 Guests
1 Bedroom
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $2,500/Night
For 7 Nights US $17,500
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $512/Night
For 7 Nights US $3,581
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $497/Night
For 7 Nights US $3,480
1386 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $499/Night
For 7 Nights US $3,494
Upper Matecumbe Key Luxury Rentals
Unlock the Best Price
10763.91 ft²
15 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Beach
- Oceanfront
- Fireplace/Heating
US $7,615/Night
For 7 Nights US $53,305
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
US $6,474/Night
For 7 Nights US $45,320
3772 ft²
16 Guests
6 Bedrooms
6 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
US $4,807/Night
For 7 Nights US $33,646
1320 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $4,538/Night
For 7 Nights US $31,769
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Air Conditioner
- Internet
US $3,783/Night
For 7 Nights US $26,481
16 Guests
8 Bedrooms
8 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $3,709/Night
For 7 Nights US $25,960
5826 ft²
22 Guests
10 Bedrooms
10 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Fireplace/Heating
US $3,453/Night
For 7 Nights US $24,174
Upper Matecumbe Key Pet Friendly Vacation Rentals
1100 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Ocean View
- Balcony/Terrace
- View
US $313/Night
For 7 Nights US $2,189
436.91 ft²
68 Guests
107 Bedrooms
22 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
US $710/Night
For 7 Nights US $4,971
US $274/Night
For 7 Nights US $1,918
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $269/Night
For 7 Nights US $1,886
418.14 ft²
69 Guests
88 Bedrooms
18 Bathrooms
Resort
- Private Beach
- Oceanfront
- Fireplace/Heating
US $649/Night
For 7 Nights US $4,543
2000 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $465/Night
For 7 Nights US $3,252
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $723/Night
For 7 Nights US $5,064
980 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
US $358/Night
For 7 Nights US $2,509
Upper Matecumbe Key Large Vacation Homes
1380 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Pool
US $393/Night
For 7 Nights US $2,751
1302.43 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Villa
- Private Beach
- Oceanfront
- Pool
US $495/Night
For 7 Nights US $3,465
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Pool
- Ocean View
- Balcony/Terrace
US $624/Night
For 7 Nights US $4,371
1582.29 ft²
12 Guests
5 Bedrooms
4 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
US $180/Night
For 7 Nights US $1,260
850 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
US $450/Night
For 7 Nights US $3,150
1600 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Pool
- Ocean View
US $451/Night
For 7 Nights US $3,156
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Pool
US $538/Night
For 7 Nights US $3,764
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Hot Tub
- Fireplace/Heating
- Ocean View
US $518/Night
For 7 Nights US $3,623
Why Choose Rent By Owner for your Upper Matecumbe Key Vacation Rental Homes?
What makes our Vacation Rentals 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 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 636+ 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.
Average Temperature Daytime: around 80°F - Nighttime: approximately 70°F
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.
Average Temperature Daytime: about 75°F - Nighttime: roughly 65°F
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.
Average Temperature Daytime: around 88°F - Nighttime: about 78°F
Fall (September to November)
As the region transitions into fall, the weather cools slightly, and fewer visitors mean more tranquil surroundings for your stay.
Average Temperature Daytime: approximately 82°F - Nighttime: around 72°F
Weekly Weather Forecast for Upper Matecumbe Key
How to Book Your Upper Matecumbe Key Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
- 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
History of Diving Museum
Islamorada
Matecumbe United Methodist Church
Florida Keys Brewing Co.
Hurricane Monument
Coral Cove
Bud n' Mary's Dive Center
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.
Upper Matecumbe Key Vacation Rental Frequently Asked Questions
1. 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:
- ISLAMORADA, ANGLERS REEF PRISTINE HOME Pool, Dock, Beach, Kayaks, Paddle Boards
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Oceanside Getaway: Beautiful Home with Boat Slip, Pool & Beach - Gated community
- The Caribbean Resort
- AQUAMARINE OCEANVIEW+”SPECIAL RATES”+nDOCK+POOL+GYM+SPA+”153”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
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
2. How many vacation rentals have private pools in Upper Matecumbe Key?
There are 200 vacation rentals with private pools near Upper Matecumbe Key. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Upper Matecumbe Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1387 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.
5. What is the cancellation policy for vacation rentals in Upper Matecumbe Key, Florida?
Cancellation policies vary by listing. You should review the specific property's cancellation terms on the booking page or contact the property owner directly to understand your options and potential fees.
6. How do I find available vacation rentals in Upper Matecumbe Key with flexible booking options?
Use the search filters on the booking platform to set your preferred dates and select options such as free cancellation or flexible check-in, which are often highlighted in the listing details.
7. Are there any additional fees or charges when booking a vacation rental in this part of Florida?
Additional fees like cleaning, service charges, or taxes are typically included in the listing's total price but always review the detailed fee breakdown on the property page before confirming your reservation.
8. What amenities are generally included in vacation rentals in Upper Matecumbe Key?
Most rentals offer essentials like Wi-Fi, parking, and kitchen facilities, but amenities can vary. Check each listing’s description to ensure it meets your needs before booking.
9. How do I communicate special requests or specific questions about a vacation rental in the area?
You can contact the property owner directly through the messaging feature on the booking platform to ask about special accommodations, house rules, or other concerns prior to completing your reservation.
Upper Matecumbe Key Top Rated Vacation Rentals
US $639/Night
For 7 Nights US $4,473
1700 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $445/Night
For 7 Nights US $3,114
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $338/Night
For 7 Nights US $2,366
2200 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $1,350/Night
For 7 Nights US $9,450
1980 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $902/Night
For 7 Nights US $6,315
2200 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $817/Night
For 7 Nights US $5,716
1928 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $808/Night
For 7 Nights US $5,653
2450 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,872/Night
For 7 Nights US $13,106
