Compare Cheap Hotels in Upper Matecumbe Key
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Cheap Upper Matecumbe Key Hotels
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$239 nightly
The price is $269 total per night
$269 total
Dec 22 - Dec 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
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 Park.
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$321 nightly
The price is $361 total per night
$361 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
1.88 mi from city center
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 Co..
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$364 nightly
The price is $410 total per night
$410 total
Dec 19 - Dec 20
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.09 mi from city center
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 Keys Brewing Co..
Islander Resort
82100 Overseas Highway Islamorada FL
$340 nightly
The price is $383 total per night
$383 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.33 mi from city center
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 & Distillery.
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
$178 nightly
The price is $200 total per night
$200 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
0.82 mi from city center
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 Museum.
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$328 nightly
The price is $369 total per night
$369 total
Dec 23 - Dec 24
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.52 mi from city center
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 Center.
Sunset Inn
82200 Overseas Hwy Islamorada FL
$171 nightly
The price is $193 total per night
$193 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
0.39 mi from city center
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 & Discovery Center.
La Jolla Resort
82216 Overseas Highway Islamorada FL
$145 nightly
The price is $163 total per night
$163 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
0.5 mi from city center
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 Center.
Pines & Palms Resort
80401 Old Hwy Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
1.46 mi from city center
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 n' Mary's Dive Center.
The Islands of Islamorada
82779 Old Hwy Islamorada FL
$658 nightly
The price is $740 total per night
$740 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
0.94 mi from city center
With a stay at The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery.
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$171 nightly
The price is $192 total per night
$192 total
Dec 21 - Dec 22
Total with taxes and fees
1.81 mi from city center
With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park.
Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
$374 nightly
The price is $421 total per night
$421 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
0.67 mi from city center
With a stay at Bayside Villas by Islander Resort, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co..
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Upper Matecumbe Key hotels essential information
Accommodation | 2,810 hotels |
|---|---|
Lowest Price | $163 |
Highest Price | $740 |
Popular hotels | Chesapeake Beach Resort, Amara Cay Resort, Cheeca Lodge & Spa, Islander Resort, Hadley Resort and Marina, La Siesta Resort & Villas, Sunset Inn, La Jolla Resort, Pines & Palms Resort, The Islands of Islamorada, Breezy Palms Resort, Bayside Villas by Islander Resort |
Most Recent Upper Matecumbe Key Hotel Reviews
Pines & Palms Resort
5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"Staff are excellent, resort has been recently upgraded. Best describe his quaint, comfortable and cozy."
A verified traveler stayed at Pines & Palms Resort
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