Compare Cheap Hotels in Upper Matecumbe Key

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Cheap Upper Matecumbe Key Hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$214 nightly
The price is $241 total per night
$241 total
Aug 27 - Aug 28
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..
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
$209 nightly
The price is $235 total per night
$235 total
Aug 25 - Aug 26
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
$252 nightly
The price is $283 total per night
$283 total
Aug 26 - Aug 27
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$304 nightly
The price is $342 total per night
$342 total
Sep 22 - Sep 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
$224 nightly
The price is $252 total per night
$252 total
Aug 30 - Aug 31
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 3-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center.
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$237 nightly
The price is $266 total per night
$266 total
Aug 26 - Aug 27
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 a 4-minute walk from Indian Key Historic State Park and 11 minutes by foot from Bud n' Mary's Dive Center.
On private beach
Pool
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
$158 nightly
The price is $178 total per night
$178 total
Sep 7 - Sep 8
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
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
$128 nightly
The price is $144 total per night
$144 total
Sep 1 - Sep 2
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.
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$144 nightly
The price is $162 total per night
$162 total
Aug 27 - Aug 28
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
$416 nightly
The price is $467 total per night
$467 total
Sep 22 - Sep 23
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
Casa Morada

Casa Morada

3.5 out of 5
82200 overseas HWY Islamorada FL
$194 nightly
The price is $218 total per night
$218 total
Aug 31 - Sep 1
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.41 mi from city center
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Islamorada Brewery & Distillery and Lorelei Restaurant & Cabana Bar are located nearby.
The Caribbean Resort

The Caribbean Resort

3.5 out of 5
117 Carroll St Islamorada FL
0.14 mi from city center
A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum.
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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
2,761 hotels
Lowest Price
$144
Highest Price
$467
Popular hotels
Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, Islander Resort, Pines & Palms Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Breezy Palms Resort, La Jolla Resort, The Islands of Islamorada, Casa Morada, The Caribbean Resort

Most Recent Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

5 out of 5
Posted 8 hours ago
CheapTickets Verified Review
"We had a wonderful stay at the Islander Resort in Islamorada! The property is beautiful, relaxing, and has that perfect Florida Keys atmosphere. The grounds are very well maintained, the pools are great, and the oceanfront setting makes it easy to relax and enjoy the gorgeous views. Our room was comfortable and clean, and we really enjoyed the resort amenities. The food and drinks were excellent, and it was so convenient to have everything we needed right on the property. The staff was friendly and welcoming throughout our stay. The location is also fantastic—close to some of our favorite restaurants and everything Islamorada has to offer, while still feeling peaceful and tropical once you’re at the resort. Highly recommend Squares Grouper for dinner, Green Turtle Inn for breakfast. We had such an enjoyable and relaxing getaway and would definitely stay at the Islander Resort again. Highly recommend it for anyone looking for a beautiful Keys vacation!"
A verified traveler stayed at Islander Resort
Islander Resort

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