Upper Matecumbe Key Cabin Rentals
House
2 Bedrooms
2 Baths
4 Guests
Fireplace/Heating
Pet Friendly
Kitchen
Parking
US $280/Night
7 Nights - US $1,961
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1679.17 ft²
Spa
Pool
View
Breakfast
US $966/Night
7 Nights - US $6,762
House
9.6(246 Reviews)
1 Bedroom
1 Bath
- Pool
Ocean View
Balcony/Terrace- View
US $258/Night
7 Nights - US $1,807
New
Condo
1 Bedroom
1 Bath
4 Guests
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
US $159/Night
7 Nights - US $1,115
House
10.0(1 Review)
1 Bedroom
5 Baths
10 Guests
10.76 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $2,500/Night
7 Nights - US $17,500
House
10.0(192 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $454/Night
7 Nights - US $3,181
House
9.6(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
1550 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
US $400/Night
7 Nights - US $2,800
House
10.0(188 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $476/Night
7 Nights - US $3,331
Apartment
9.5(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,324
Condo
10.0(158 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Pool
US $404/Night
7 Nights - US $2,831
House
9.5(4 Reviews)
2 Bedrooms
1 Bath
5 Guests
527.43 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $308/Night
7 Nights - US $2,156
House
10.0(146 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $363/Night
7 Nights - US $2,543
Why Choose Rent By Owner for your Upper Matecumbe Key Cabin Rentals?
What makes our Cabin 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.
Weekly Weather Forecast for Upper Matecumbe Key
How to Book Your Upper Matecumbe Key Cabin Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cabin 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 Cabin Rentals Amenities
What amenities can you expect?
Our Cabin 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
Other Places to Stay in Upper Matecumbe Key, FL
History of Diving Museum
Matecumbe United Methodist Church
Florida Keys Brewing Co.
Hurricane Monument
Islamorada
Coral Cove
Bud n' Mary's Dive Center
Frequently Asked Questions About Upper Matecumbe Key Rental Cabins
1. What are the top Cabins 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 Cabins in Upper Matecumbe Key:
- The Caribbean Resort
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
- Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
- Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
- Truly OceanFRONT-PanoramicOceanViews-WraparoundDecks-QuietLocation-AvailableSlip
- Next available - August 2026 - Oceanfront - Heated Pool - Dock
- Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
- Anglers Reef Islamorada home with ocean views, private marina, beach & pool
2. How many Cabins are available in Upper Matecumbe Key?
Currently, the total number of properties listed by RBO in 2026 is over 1398 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 Cabins in Upper Matecumbe Key.
More Rentals You May Like Near Upper Matecumbe Key
Villa
9.5(2 Reviews)
2 Bedrooms
3 Baths
6 Guests
1302.43 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
US $495/Night
7 Nights - US $3,465
Cottage
10.0(138 Reviews)
1 Bedroom
1 Bath
2 Guests
1100 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
US $333/Night
7 Nights - US $2,334
Villa
10.0(122 Reviews)
2 Bedrooms
2 Baths
6 Guests
1380 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $393/Night
7 Nights - US $2,751
Cottage
10.0(114 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $269/Night
7 Nights - US $1,886
House
10.0(110 Reviews)
2 Bedrooms
2 Baths
4 Guests
1550 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $387/Night
7 Nights - US $2,710
House
10.0(105 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $650/Night
7 Nights - US $4,552
Apartment
10.0(102 Reviews)
2 Bedrooms
2 Baths
8 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $465/Night
7 Nights - US $3,252
House
10.0(100 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $635/Night
7 Nights - US $4,442
House
10.0(95 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $673/Night
7 Nights - US $4,712
Villa
10.0(95 Reviews)
2 Bedrooms
2 Baths
4 Guests
980 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $342/Night
7 Nights - US $2,396
House
10.0(91 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $445/Night
7 Nights - US $3,116
House
10.0(88 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $524/Night
7 Nights - US $3,670
