Book Cheap Hotels in Upper Matecumbe Key
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Tomorrow night
Check prices in Upper Matecumbe Key for tomorrow night, Jun 14 - Jun 15Most 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 $334 per night
CA $334
CA $478 total
Jun 14 - Jun 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.
On private beach
Pool

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 $234 per night
CA $234
CA $341 total
Jun 14 - Jun 15
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
Free cancellation
Reserve now, pay when you stay
0.37 km from city centre
The price is CA $357 per night
CA $357
CA $496 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 $242 per night
CA $242
CA $375 total
Jul 8 - Jul 9
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 $246 per night
CA $246
CA $379 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.
On private beach
Pool

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 $328 per night
CA $328
CA $463 total
Jun 24 - Jun 25
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.
Pool
Pet-friendly

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 $164 per night
CA $164
CA $207 total
Jun 14 - Jun 15
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 $207 |
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

Pines & Palms Resort
5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Very clean and a great place to stay to happy hours the best four dollar drinks can't be that"
A verified traveller stayed at Pines & Palms Resort
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