Upper Matecumbe Key Rentals By Owner

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:

• Truly OceanFRONT-PanoramicOceanViews-WraparoundDecks-QuietLocation-AvailableSlip
• 5 Star Modern Oceanfront Islamorada Townhome on the Beach!
• Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
• Next availability May 2nd 2026 - Booking 2027 Oceanfront - Heated Pool - Dock
• Stunning Bayfront Townhouse with Boat Slip/Marina Access - A Luxurious Retreat!
• Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
• Anglers Reef Islamorada Ocean Views DOCK Beach Pool Boat Slip NO ROAD NOISE!
• Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
• Anglers Reef Islamorada home with ocean views, private marina, beach & pool
• Stunning Oceanfront Home located in Islamorada Florida

There are many large, family-friendly vacation homes available in Upper Matecumbe Key; however, here are the most popular family rentals listed on our site:

• ISLAMORADA, ANGLERS REEF PRISTINE HOME Pool, Dock, Beach, Kayaks, Paddle Boards
• Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
• The Islands of Islamorada
• Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

Yes, there are 1063 self-catering vacation homes in Upper Matecumbe Key that have hot tubs, swimming pools, & other amenities.

There are more than 1063 luxury villas and vacation homes in or near Upper Matecumbe Key. Filter by price to compare find the most expensive places to stay on Toodoo.

Yes, there are 1063 pet friendly vacation homes and places to stays that are available in or near Upper Matecumbe Key that you may consider.