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 €129 for one-way flights and €268 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
€1,095

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Featured Hotels near Upper Matecumbe Key

Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is €299 per night from 19 Jul to 20 Jul
€299
19 Jul - 20 Jul
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. This property offers pet-friendly amenities, such as food and water bowls.
9.4/10 Exceptional! (1,055 reviews)
"The resort is absolutely beautiful! The room is immaculate , and you even have a walk out patio . Two pools, one for relaxation and the other for “kids” I am impressed at this resort."

Reviewed on 18 Jun 2026

Opens in a new windowIslander Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €298 per night from 13 Jul to 14 Jul
€298
13 Jul - 14 Jul
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! (1,319 reviews)
"There was a lot of seaweed, which definitely had an odor; it was impossible to use the beach area. I did expect they would make more of an effort to clean it. Could use some TCL, adult pool needs new steps that do not get too hot to touch in the summertime. (They make them now). Could have made more ..."

Reviewed on 18 Jun 2026

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is €244 per night from 21 Jun to 22 Jun
€244
21 Jun - 22 Jun
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! (1,733 reviews)
"We had a fabulous stay, would stay again!!"

Reviewed on 20 Jun 2026

Opens in a new windowChesapeake Beach Resort
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Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway Islamorada FL
The price is €306 per night from 29 Jun to 30 Jun
€306
29 Jun - 30 Jun
includes taxes & fees
During your stay at Bayside Villas by Islander Resort, you're just a quick walk from Hurricane Monument. Features include free WiFi in public areas, free self-parking and a free area shuttle.
9/10 Wonderful! (443 reviews)
"The property was in excellent condition. Roomy accommodations for a family. Lots of activities within a 50-mile radius for children."

Reviewed on 15 Jun 2026

Opens in a new windowBayside Villas by Islander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is €248 per night from 6 Jul to 7 Jul
€248
6 Jul - 7 Jul
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! (1,287 reviews)
"The lobby seating is very dirty."

Reviewed on 19 Jun 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 €255 per night from 6 Jul to 7 Jul
€255
6 Jul - 7 Jul
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)
"Service great room great room service good breakfast big room, nice pool, friendly staff great views amazing views I used voice text so I’m sorry this makes no sense. Will be staying again it was my second time here."

Reviewed on 17 Jun 2026

Opens in a new windowLa Siesta Resort & Villas
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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.