Owner Direct Vacation
Rentals in Upper Matecumbe Key
The Best Owner Direct Vacation Rentals in Upper Matecumbe Key. Explore thousands of vacation home rentals, large cabins, and villas near Upper Matecumbe Key
GUESTS
Explore the Best Upper Matecumbe Key Vacation Homes
Looking for the perfect place to stay in Upper Matecumbe Key? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Upper Matecumbe Key character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pool
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Parking
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Parking
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pool
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Why Travelers Love Using
Owner Direct to
Find Upper Matecumbe Key Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Upper Matecumbe Key
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pool
- View
- Air Conditioner
- Parking
- Pool
Popular Neighborhoods for Upper Matecumbe Key Vacation Rentals
What are the best areas to stay in Upper Matecumbe Key
Discover the top neighborhoods in Upper Matecumbe Key and choose a place that suits your stay.
Sunday Feb 8
Upper Matecumbe Key, Florida
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Upper Matecumbe Key vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Upper Matecumbe Key
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pool
- Wheelchair Accessible
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
How to Reserve Your Upper Matecumbe Key Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Upper Matecumbe Key Vacation Rental FAQs
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: Renovated 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!
- Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
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 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 vacation rentals are available in Upper Matecumbe Key?
Currently, the total number of properties listed in 2026 is over 1371 in the Upper Matecumbe Key area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Upper Matecumbe Key.