Compare Cheap Hotels in Upper Matecumbe Key

Name: The Islands of Islamorada
Price range: $719 total

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Cheap Upper Matecumbe Key Hotels

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$264 nightly

$297 total

Nov 19 - Nov 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 steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing Co..

On private beach

Pool

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

$201 nightly

$226 total

Oct 26 - Oct 27

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

80001 Overseas Hwy Islamorada FL

$252 nightly

$283 total

Nov 15 - Nov 16

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

82100 Overseas Highway Islamorada FL

$258 nightly

$290 total

Nov 15 - Nov 16

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

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

$123 nightly

$139 total

Oct 21 - Oct 22

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

La Jolla Resort

82216 Overseas Highway Islamorada FL

$168 nightly

$189 total

Oct 22 - Oct 23

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

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

$224 nightly

$252 total

Nov 15 - Nov 16

Total with taxes and fees

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

82749 Overseas Hwy Islamorada FL

$168 nightly

$189 total

Oct 21 - Oct 22

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

Casa Morada

82200 overseas HWY Islamorada FL

$184 nightly

$207 total

Oct 27 - Oct 28

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

0.41 mi from city center

With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 6 minutes by foot from Lorelei Restaurant & Cabana Bar.

Pool

Pet friendly

Pines & Palms Resort

80401 Old Hwy Islamorada FL

$288 nightly

$324 total

Nov 19 - Nov 20

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.

On private beach

Pool

The Caribbean Resort

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.

Pool

Hot Tub

The Islands of Islamorada

82779 Old Hwy Islamorada FL

$641 nightly

$719 total

Oct 22 - Oct 23

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

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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	2,739 hotels
Lowest Price	$139
Highest Price	$719
Popular hotels	Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, Islander Resort, Breezy Palms Resort, La Jolla Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Casa Morada, Pines & Palms Resort, The Caribbean Resort, The Islands of Islamorada

Most Recent Upper Matecumbe Key Hotel Reviews

Islander Resort

5 out of 5

Posted 3 hours ago

CheapTickets Verified Review

"Resort was always clean during our stay. All of the staff were incredibly nice and helpful! Lots of activities on the property to keep you entertained."

A verified traveler stayed at Islander Resort