Compare Cheap Hotels in Upper Matecumbe Key

Secret Bargains - Save an extra 10% or more on select hotels

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cheap Upper Matecumbe Key Hotels

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is $267 per night
$267
includes taxes & fees
$237 per night
Nov 17 - Nov 18
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..
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is $211 per night
$211
includes taxes & fees
$194 per night
Dec 11 - Dec 12
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

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is $248 per night
$248
includes taxes & fees
$220 per night
Nov 17 - Nov 18
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 13 minutes by foot from Indian Key Historic State Park.
On private beach
Pool
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
The price is $250 per night
$250
includes taxes & fees
$222 per night
Nov 19 - Nov 20
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is $262 per night
$262
includes taxes & fees
$232 per night
Nov 20 - Nov 21
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

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
The price is $175 per night
$175
includes taxes & fees
$156 per night
Nov 20 - Nov 21
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.
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy, Islamorada, FL
The price is $162 per night
$162
includes taxes & fees
$144 per night
Nov 20 - Nov 21
Free Cancellation
Reserve now, pay when you stay
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.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway, Islamorada, FL
The price is $172 per night
$172
includes taxes & fees
$155 per night
Nov 21 - Nov 22
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.
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway, Islamorada, FL
The price is $140 per night
$140
includes taxes & fees
$124 per night
Nov 17 - Nov 18
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.
Sands of Islamorada

Sands of Islamorada

2.5 out of 5
80051 Overseas Highway, Islamorada, FL
The price is $204 per night
$204
includes taxes & fees
$181 per night
Nov 17 - Nov 18
1.78 mi from city center
Located in Islamorada (Matecumbe), Sands of Islamorada is within a 5-minute drive of Bud n' Mary's Dive Center and History of Diving Museum.
Islander Bayside Villas and Boatslips

Islander Bayside Villas and Boatslips

3.5 out of 5
81450 Overseas Highway, Islamorada, FL
The price is $265 per night
$265
includes taxes & fees
$235 per night
Nov 20 - Nov 21
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
With a stay at Islander Bayside Villas and Boatslips, 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..
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy, Islamorada, FL
The price is $308 per night
$308
includes taxes & fees
$274 per night
Dec 15 - Dec 16
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.
Don't see what you're looking for?
See all available properties in Upper Matecumbe Key
View all properties
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.

Often, one of the most difficult things about booking a hotel is finding the best time to go. The cost of staying in hotels in could vary significantly, depending on the time of the year chosen. If you would like to figure out the most suitable time to take a trip then using CheapTickets could be the best option for you. We will be able to provide information on hotels in to ensure that you get the best deal possible. So if you are looking for a booking website that will streamline the process and offer good prices, then log in and get booking.

Upper Matecumbe Key hotels essential information

Accommodation
2,733 hotels
Lowest Price
$140
Highest Price
$308
Popular hotels
Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort, La Siesta Resort & Villas, Islander Resort, Hadley Resort and Marina, Sunset Inn, Breezy Palms Resort, La Jolla Resort, Sands of Islamorada, Islander Bayside Villas and Boatslips, Pines & Palms Resort

Most Recent Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Amazing property! We had a reservation at a different place and were not happy with it so decided to push on. We couldn’t be happier. The staff is amazing, breakfast is great and there is a private beach. We are so happy we extended our stay."
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort