Book Hotels in Upper Matecumbe Key, FL
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Check prices in Upper Matecumbe Key for tomorrow night, Jun 19 - Jun 20Top Upper Matecumbe Key hotels

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.88 mi from city center
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle. You'll appreciate the gym, poolside bar, and laundry facilities.
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
0.09 mi from city center
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a playground, and families will appreciate the onsite laundry facilities.
On private beach
Pool

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.76 mi from city center
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at the bar/lounge and enjoy perks like free continental breakfast and free WiFi.
On private beach
Pool

Islander Resort
82100 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.33 mi from city center
This hotel features a private beach, a golf course, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the mini golf and complimentary bicycles.
On private beach
Pool

La Siesta Resort & Villas
80241 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
1.52 mi from city center
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, and a 24-hour front desk and wedding services are also provided.
On private beach
Pool

Hadley Resort and Marina
82749 Overseas Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.82 mi from city center
This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate the playground and barbecue grills.
On private beach
Pool

La Jolla Resort
82216 Overseas Highway, Islamorada, FL
0.5 mi from city center
A private beach and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are also on offer.
On private beach
Pool

The Islands of Islamorada
82779 Old Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
0.94 mi from city center
2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Families will appreciate the playground and barbecue grills.
Pool
Hot Tub
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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.
Hotels in Upper Matecumbe Key with star-rating
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5 Star Hotels
3 properties
Top hotels in Upper Matecumbe Key for Extended Stay

Island Bay Resort
92530 OVERSEAS HIGHWAY, Key Largo, Tavernier, FL
9.8/10 Exceptional! (119 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 | 2,755 hotels |
---|---|
Lowest Price | |
Highest Price | |
Popular hotels | Amara Cay Resort, Cheeca Lodge & Spa, Chesapeake Beach Resort, Islander Resort, La Siesta Resort & Villas, Hadley Resort and Marina, La Jolla Resort, The Islands of Islamorada, Islander Bayside Villas and Boatslips |
Recent Upper Matecumbe Key hotel reviews by fellow wanderers

Hadley Resort and Marina
5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"I have no complaints. We would definitely stay here again."
A verified traveler stayed at Hadley Resort and Marina
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