Lakes Resorts - Vacation Rentals in Upper Matecumbe Key

Keys Villa From US $364
         

10.0 (8 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Cheeca Lodge & Spa From US $378
         

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9.2 (1333 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL From US $371
         

9.4 (3 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Upper Matecumbe Key

Over 1433+ Luxury Places to Stay in or Near Upper Matecumbe Key
New
House
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10 Bedroom Private Ocean Front Estate From US $3,453
         

10.0 (1 Review)
Villa
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  • Parking
  • Pool
Oceanfront 4BR Villa | Resort Access + Bunks From US $2,945
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Upper Matecumbe Key

Over 1042+ Top-Rated Vacation Rentals with a Pool in or Near Upper Matecumbe Key
The Caribbean Resort From US $639
         

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10.0 (172 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Designated Smoking Area
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,322
         

Serenity by the Sea! Anglers Reef with Boat Slip Available! From US $393
         

Pet-Friendly Vacation Rentals in Upper Matecumbe Key

Over 450+ Pet-Friendly Vacation Rentals in or Near Upper Matecumbe Key
Hooked on Islamorada Oceanfront Townhome, Private Dock, Pool From US $764
         

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9.5 (2 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Fisher Inn Resort & Marina From US $206
         

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8.2 (1010 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Oceanfront Private Cottage! From US $269
         

10.0 (116 Reviews)
Cottage
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  • Parking
  • Pet Friendly
Breathtaking ocean views for your Paradise vacations From US $465
         

10.0 (104 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Next available - August 2026 - Oceanfront - Heated Pool - Dock From US $1,283
         

10.0 (98 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Upper Matecumbe Key

Over 278+ Large Vacation Homes & Villas in or Near Upper Matecumbe Key
Pineapple Beach From US $2,500
         

10.0 (1 Review)
House
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  • Pool
The Islands of Islamorada From US $774
         

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9.6 (76 Reviews)
Villa
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Islamorada house with best location. Lic # 24-0055 From US $624
         

10.0 (21 Reviews)
Villa
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Isla Honeydew: 3 En-Suite Bedrooms, Pool, Dock From US $457
         

10.0 (8 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Upper Matecumbe Key

Over 418+ Wheelchair Accessible Vacation Homes in or Near Upper Matecumbe Key
Islander Resort From US $710
         

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8.9 (1338 Reviews)
Resort
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  • Pet Friendly
Bayside Villas by Islander Resort From US $368
         

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9.0 (437 Reviews)
Hotel
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  • Pool
Ocean & Bay Views. Welcome To Paradise! From US $358
         

10.0 (36 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Egret House @ Tarpon Point From US $973
         

10.0 (22 Reviews)
House
  • Air Conditioner
  • Pool
  • TV
Islamorada Penthouse with Private Beach & Pool! From US $904
         

10.0 (21 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Upper Matecumbe Key Vacation Rentals and Airbnb Places to Stay Under $200

Over 112+ Upper Matecumbe Key Vacation Rentals and Airbnb Places to Stay Under $200
Islamorada Paradise Overlooking the Fabulous Florida Bay. From US $189
         

Breezy Palms Resort From US $195
         

8.8 (697 Reviews)
Apartment
  • Air Conditioner
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  • Pool
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball From US $128
         

Beach View Unit in Islamorada! Pets Allowed, Parking, Pool! From US $190
         

8.6 (26 Reviews)
Apartment
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  • Pet Friendly
Keys Cottage Downtown Islamorada — walk From US $197
         

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  • Pet Friendly
  • Security/Safety

Instantly Bookable Vacation Homes in Upper Matecumbe Key

Over 760+ Instantly Bookable Vacation Homes in or Near Upper Matecumbe Key
Anglers Reef Islamorada - 2:2.5, Boat Slip, Pool & Beach From US $416
         

About Upper Matecumbe Key Vacation Rentals

With more than 78 Upper Matecumbe Key vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Lakesresorts and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Upper Matecumbe Key.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Lakesresorts Upper Matecumbe Key, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Upper Matecumbe Key. Places to stay near Upper Matecumbe Key are 653.16 ft² on average, with prices averaging US $632 a night.

Lakesresorts makes it easy and safe to find and compare vacation rentals in Upper Matecumbe Key with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Upper Matecumbe Key

Type Count
Resorts 60
Hotels 8
Villas 6
Vacation Homes 3
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Upper Matecumbe Key

Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Upper Matecumbe Key.

Weather in Upper Matecumbe Key

View the weather forecast for Upper Matecumbe Key before booking your Upper Matecumbe Key Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Upper Matecumbe Key Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Upper Matecumbe Key?
How many vacation rentals are available in Upper Matecumbe Key?

Currently, the total number of properties listed in 2026 is over 78 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.