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
$239 nightly
The price is $269 total per night
$269 total
Jun 16 - Jun 17
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
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$304 nightly
The price is $342 total per night
$342 total
Jun 29 - Jun 30
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 steps 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
$316 nightly
The price is $356 total per night
$356 total
Jun 22 - Jun 23
Total with taxes and fees
0.23 mi from city center
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 4 minutes by foot from Lorelei Restaurant & Cabana Bar.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$274 nightly
The price is $309 total per night
$309 total
Jul 6 - Jul 7
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
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$260 nightly
The price is $293 total per night
$293 total
Jul 6 - Jul 7
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
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway Islamorada FL
$305 nightly
The price is $343 total per night
$343 total
Jun 23 - Jun 24
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
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
$175 nightly
The price is $197 total per night
$197 total
Jun 16 - Jun 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 Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$214 nightly
The price is $241 total per night
$241 total
Jun 21 - Jun 22
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 9 minutes by foot from Lorelei Restaurant & Cabana Bar.
On private beach
Pool
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
$688 nightly
The price is $774 total per night
$774 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
$176 nightly
The price is $198 total per night
$198 total
Jun 25 - Jun 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.82 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
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$180 nightly
The price is $203 total per night
$203 total
Jul 1 - Jul 2
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 5 minutes by foot from Lorelei Restaurant & Cabana Bar.
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
$308 nightly
The price is $347 total per night
$347 total
Jun 16 - Jun 17
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
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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.

Upper Matecumbe Key hotels essential information

Accommodation
2,776 hotels
Lowest Price
$197
Highest Price
$774
Popular hotels
Chesapeake Beach Resort, Cheeca Lodge & Spa, Islander Resort, Amara Cay Resort, La Siesta Resort & Villas, Bayside Villas by Islander Resort, Hadley Resort and Marina, La Jolla Resort, The Islands of Islamorada, Breezy Palms Resort, Sunset Inn, Pines & Palms Resort

Most Recent Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5 out of 5
Posted less than an hour ago
CheapTickets Verified Review
"Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here."
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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