Book Cheap Hotels in Upper Matecumbe Key
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Tomorrow night
Check prices in Upper Matecumbe Key for tomorrow night, Jun 15 - Jun 16Most frequently booked Upper Matecumbe Key hotels

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free cancellation
Reserve now, pay when you stay
0.14 km from city centre
The price is CA $284 per night
CA $284
CA $422 total
Jul 14 - Jul 15
includes taxes & fees
Book a stay at this 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 Florida Keys Brewing Co. and MoradaWay Arts & Cultural District are located nearby.

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 $249 per night
CA $249
CA $358 total
Jun 18 - Jun 19
includes taxes & fees
Book a stay at this 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.

Islander Resort
82100 Overseas Highway Islamorada FL
0.37 km from city centre
The price is CA $358 per night
CA $358
CA $497 total
Jun 21 - Jun 22
includes taxes & fees
Book a stay at this 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.

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 $254 per night
CA $254
CA $388 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.

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 $243 per night
CA $243
CA $376 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this 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.

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 $184 per night
CA $184
CA $252 total
Jun 17 - Jun 18
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 Florida Keys Brewing Company and Islamorada Brewery & Distillery are located nearby.

Bayside Villas by Islander Resort
81450 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
1.08 km from city centre
The price is CA $338 per night
CA $338
CA $475 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Hurricane Monument and MoradaWay Arts & Cultural District are located nearby.

La Jolla Resort
82216 Overseas Highway Islamorada FL
0.8 km from city centre
The price is CA $238 per night
CA $238
CA $307 total
Jun 21 - Jun 22
includes taxes & fees
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 Florida Keys Brewing Company are located nearby.

Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
2.93 km from city centre
The price is CA $168 per night
CA $168
CA $261 total
Jul 1 - Jul 2
includes taxes & fees
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
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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 Tavernier FL
The price is CA $372 per night from Jul 1 to Jul 2
CA $372
CA $419 total
Jul 1 - Jul 2
includes taxes & fees
10/10 Exceptional! (170 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 | 2,788 hotels |
|---|---|
Lowest Price | CA $252 |
Highest Price | CA $2,864 |
Popular hotels | Cheeca Lodge & Spa, Chesapeake Beach Resort, Islander Resort, Amara Cay Resort, La Siesta Resort & Villas, Hadley Resort and Marina, Bayside Villas by Islander Resort, La Jolla Resort, Breezy Palms Resort |
Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Cheeca Lodge & Spa
4 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Property and room are beautiful, up to date and well-maintained. Secluded and calm as well. In-house dining was 6.5/10, concierge attitude was subpar and room service the first night was not good, second room service took an hour and a half ."
A verified traveller stayed at Cheeca Lodge & Spa
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