Book Cheap Hotels in Upper Matecumbe Key
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Tomorrow night
Check prices in Upper Matecumbe Key for tomorrow night, Aug 20 - Aug 21Most frequently booked Upper Matecumbe Key hotels

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
2.84 km from city centre
The price is CA $169 per night
CA $169
CA $268 total
Aug 27 - Aug 28
includes taxes & fees
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
On private beach
Pool

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
0.14 km from city centre
The price is CA $213 per night
CA $213
CA $333 total
Aug 20 - Aug 21
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Matecumbe United Methodist Church and Florida Keys Brewing Co. are located nearby.
On private beach
Pool

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
3.02 km from city centre
The price is CA $232 per night
CA $232
CA $353 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
On private beach
Pool

Islander Resort
82100 Overseas Highway, Islamorada, FL
0.54 km from city centre
The price is CA $265 per night
CA $265
CA $391 total
Sep 10 - Sep 11
includes taxes & fees
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Keys History & Discovery Center and Islamorada Brewery & Distillery are located nearby.
On private beach
Pool

La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
2.45 km from city centre
The price is CA $196 per night
CA $196
CA $313 total
Sep 3 - Sep 4
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
On private beach
Pool

Hadley Resort and Marina
82749 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
1.32 km from city centre
The price is CA $148 per night
CA $148
CA $212 total
Sep 1 - Sep 2
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Islamorada Brewery & Distillery and History of Diving Museum are located nearby.
On private beach
Pool

Sunset Inn
82200 Overseas Hwy, Islamorada, FL
0.63 km from city centre
The price is CA $154 per night
CA $154
CA $189 total
Aug 27 - Aug 28
includes taxes & fees
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
Pool
Pet-friendly

La Jolla Resort
82216 Overseas Highway, Islamorada, FL
0.8 km from city centre
Stay at this hotel in Islamorada. Enjoy free WiFi, a private beach, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
On private beach
Pool

The Islands of Islamorada
82779 Old Hwy, Islamorada, FL
1.52 km from city centre
The price is CA $759 per night
CA $759
CA $930 total
Aug 21 - Aug 22
includes taxes & fees
Stay at this 4-star beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery & Distillery are located nearby.
Pool
Hot tub
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See all available properties in Upper Matecumbe Key
View all propertiesLowest 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.
Top hotels in Upper Matecumbe Key for Extended Stay

Island Bay Resort
92530 OVERSEAS HIGHWAY, Key Largo, Tavernier, FL
9.8/10 Exceptional! (129 reviews)
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 | 2,756 hotels |
---|---|
Lowest Price | CA $108 |
Highest Price | CA $759 |
Popular hotels | Chesapeake Beach Resort, Cheeca Lodge & Spa, Amara Cay Resort, Islander Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Sunset Inn, La Jolla Resort, The Islands of Islamorada |
Recent Upper Matecumbe Key hotel reviews by fellow wanderers

La Siesta Resort & Villas
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Definitely I will come back!!"
A verified traveller stayed at La Siesta Resort & Villas
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