Compare Cheap Hotels in Upper Matecumbe Key

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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
$192 nightly
The price is $215 total per night
$215 total
Dec 17 - Dec 18
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.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$261 nightly
The price is $293 total per night
$293 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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..
On private beach
Pool
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$259 nightly
The price is $291 total per night
$291 total
Dec 14 - Dec 15
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..
On private beach
Pool
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$396 nightly
The price is $446 total per night
$446 total
Jan 6 - Jan 7, 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.
On private beach
Pool
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
$160 nightly
The price is $180 total per night
$180 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.
On private beach
Pool
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Dec 14 - Dec 15
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.
On private beach
Pool
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$134 nightly
The price is $151 total per night
$151 total
Dec 18 - Dec 19
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.
On private beach
Pool
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$148 nightly
The price is $166 total per night
$166 total
Dec 16 - Dec 17
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.
Pool
Pet friendly
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
$248 nightly
The price is $279 total per night
$279 total
Dec 15 - Dec 16
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.
On private beach
Pool
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
$146 nightly
The price is $164 total per night
$164 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.
Pool
Kitchen
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
$648 nightly
The price is $729 total per night
$729 total
Dec 15 - Dec 16
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.
Pool
Hot Tub
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway Islamorada FL
$330 nightly
The price is $371 total per night
$371 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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..
Pool
Pet friendly
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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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Upper Matecumbe Key hotels essential information

Accommodation
2,806 hotels
Lowest Price
$151
Highest Price
$729
Popular hotels
Chesapeake Beach Resort, Amara Cay Resort, Cheeca Lodge & Spa, Islander Resort, Hadley Resort and Marina, La Siesta Resort & Villas, La Jolla Resort, Sunset Inn, Pines & Palms Resort, Breezy Palms Resort, The Islands of Islamorada, Bayside Villas by Islander Resort

Most Recent Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"The stay was excellent overall. Only issues we had was our room was full of long white flies and they didn't clean up the prior guests gross cigars on the back patio. "
A verified traveler stayed at Islander Resort
Islander Resort