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Cheap Upper Matecumbe Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$400 per night from 6 Jan to 7 Jan
AU$400
6 Jan - 7 Jan 2026
includes taxes & fees
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State ...
Opens in a new windowChesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$493 per night from 4 Jan to 5 Jan
AU$493
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing ...
Opens in a new windowAmara Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$610 per night from 4 Jan to 5 Jan
AU$610
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida ...
Opens in a new windowCheeca Lodge & Spa
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Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
Fully refundable
The price is AU$298 per night from 11 Jan to 12 Jan
AU$298
11 Jan - 12 Jan 2026
includes taxes & fees
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving ...
Opens in a new windowHadley Resort and Marina
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$840 per night from 9 Jan to 10 Jan
AU$840
9 Jan - 10 Jan 2026
includes taxes & fees
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery ...
Opens in a new windowIslander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$448 per night from 6 Jan to 7 Jan
AU$448
6 Jan - 7 Jan 2026
includes taxes & fees
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive ...
Opens in a new windowLa Siesta Resort & Villas
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 8 Jan to 9 Jan
AU$276
8 Jan - 9 Jan 2026
includes taxes & fees
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & ...
Opens in a new windowSunset Inn
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery ...
Opens in a new windowLa Jolla Resort
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud ...
Opens in a new windowPines & Palms Resort
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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.

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^Subject to availability and chosen travel dates.

Upper Matecumbe Key hotels essential information

Accommodation
2,815 hotels
Lowest Price
AU$276
Highest Price
AU$840
Popular hotels
Chesapeake Beach Resort, Amara Cay Resort, Cheeca Lodge & Spa, Hadley Resort and Marina, Islander Resort, La Siesta Resort & Villas, Sunset Inn, La Jolla Resort, Pines & Palms Resort

Most recent Upper Matecumbe Key hotel reviews

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.