Cheap flights from Upper Matecumbe Key

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Cheap round-trip flights from Upper Matecumbe Key

The lowest prices found within the past 7 days from Upper Matecumbe Key to were €62 for one-way flights and €124 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Upper Matecumbe Key Flight Information
Origin airport IATA code
MIA
Return price
€123

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Featured Hotels near Upper Matecumbe Key

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is €231 per night from 28 Jan to 29 Jan
€231
28 Jan - 29 Jan
includes taxes & fees
The free breakfast at Chesapeake Beach Resort gets high marks from our customers. During your stay, you'll be within walking distance of History of Diving Museum. Enjoy features like free WiFi in public areas, plus 2 outdoor pools and a marina.
9.2/10 Wonderful! (1,623 reviews)
The breakfast included was the best we've ever had at a hotel. Fresh omelets made to order with a wide choice of ingredients. Fresh fruit (Strawberries and blueberries ) and more. Fresh delicious muffins. The Staff was very friendly and very helpful. Would definitely recommend a stay here. The views ...

Reviewed on 9 Jan 2026

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €325 per night from 29 Jan to 30 Jan
€325
29 Jan - 30 Jan
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Cheeca Lodge & Spa. During your stay, you're just a quick walk from Matecumbe United Methodist Church. Free valet parking, 3 outdoor pools and 3 restaurants are available.
9.2/10 Wonderful! (1,283 reviews)
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.

Reviewed on 8 Jan 2026

Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is €399 per night from 13 Jan to 14 Jan
€399
13 Jan - 14 Jan
includes taxes & fees
Our customers tell us that they can't get enough of the pool at Islander Resort. During your stay, you're just a quick walk from Keys History & Discovery Center. Enjoy features like free WiFi in public areas and free self-parking, plus 2 outdoor pools.
9.2/10 Wonderful! (1,005 reviews)
So much luxury!

Reviewed on 10 Jan 2026

Opens in a new windowIslander Resort
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Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is €271 per night from 19 Jan to 20 Jan
€271
19 Jan - 20 Jan
includes taxes & fees
Our customers tell us they can't get enough of Amara Cay Resort's great location. During your stay, you're just a quick walk from Bud n' Mary's Dive Center. You'll find features such as 2 restaurants, 3 bars and an outdoor pool. This property offers pet-friendly amenities, such as food and water bowls.
8.8/10 Excellent! (1,260 reviews)
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back

Reviewed on 10 Jan 2026

Opens in a new windowAmara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is €332 per night from 13 Jan to 14 Jan
€332
13 Jan - 14 Jan
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at La Siesta Resort & Villas. During your stay, you're just a quick walk from Indian Key Historic State Park. You'll find features such as a free area shuttle, plus an outdoor pool and a marina. This property offers pet-friendly amenities, such as food and water bowls.
8.6/10 Excellent! (1,003 reviews)
Staff was very responsive. The room was great. We like having a separate room with a kitchenette and dinning table. Very quite. The other two resorts included were a plus.

Reviewed on 10 Jan 2026

Opens in a new windowLa Siesta Resort & Villas
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
The price is €197 per night from 19 Jan to 20 Jan
€197
19 Jan - 20 Jan
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Hadley Resort and Marina. During your stay, you're just a quick walk from Islamorada Brewery & Distillery. Enjoy features like free breakfast, free WiFi in public areas and free self-parking.
7.6/10 Good! (1,000 reviews)
Enjoy here and quiet place

Reviewed on 27 Dec 2025

Opens in a new windowHadley Resort and Marina
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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.