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Top Upper Matecumbe Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
1 Hotel South Beach
South Beach
Save 100% on your flight
per person
Jul. 20 - Jul. 24
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (1,004 reviews)
Very glad I chose this hotel. Staff very friendly, hotel facilities were great! fully recommend this one.
Reviewed on Jun. 3, 2024
Mayfair House Hotel & Garden
Coconut Grove
Save 100% on your flight
per person
Jul. 23 - Jul. 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (520 reviews)
What a wonderful property… beautiful rain-forest and Eco-friendly decor.. staff very helpful… great location… paid parking nearby.. very safe .. must drive to beach access
Reviewed on Jun. 2, 2024
Henrosa Hotel
South Beach
Save 100% on your flight
per person
Aug. 18 - Aug. 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
8.4/10 Very Good! (647 reviews)
Great location and so close to the beach. You can walk on Ocean drive and explore the streets without being far from the hotel.
Reviewed on Jun. 1, 2024
Upper Matecumbe Key Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $318 per night from Jun. 20 to Jun. 21
CA $318
CA $412 total
includes taxes & fees
Jun 20 - Jun 21
8.8/10 Excellent! (1,335 reviews)
"Perfect stay! Beautiful location and property!"
Reviewed on Jun. 3, 2024
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $312 per night from Jun. 4 to Jun. 5
CA $312
CA $443 total
includes taxes & fees
Jun 4 - Jun 5
8.8/10 Excellent! (1,006 reviews)
"LOVED our stay at Cheeca. We stayed in the main building this time and I can't recommend enough. The rooms were large and our children LOVED the outdoor bath/hot tub. The dining options on property are amazing as is the staff. Five stars and can't wait to go back!"
Reviewed on Jun. 1, 2024
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $368 per night from Jun. 6 to Jun. 7
CA $368
CA $490 total
includes taxes & fees
Jun 6 - Jun 7
8.8/10 Excellent! (1,240 reviews)
"We had the most relaxing time and the resort is in the best location to food and experiences! Access to La Siesta is a plus. We went during the work week, which made it a lot less crowded. I would absolutely recommend staying here to anyone!"
Reviewed on Jun. 2, 2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Discover the most popular places to visit in Upper Matecumbe Key
Everglades National Park
This sprawling wetland park holds a seemingly endless supply of wildlife habitats and enthralling ecosystems.
Theater of the Sea
4/5(6 reviews)
Swim with the dolphins and sharks and feed the crocodiles and sea turtles near the lagoon of this vast interactive park for marine mammals.
Anne's Beach
4/5(14 reviews)
If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.