Book Hotels in Upper Matecumbe Key, FL
Cabins, apartments, houseboats! We offer comfortable & private vacation rentals
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Upper Matecumbe Key hotels
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $224 total per night from Nov 15 to Nov 16
$224 total
Nov 15 - Nov 16
Total with taxes and fees
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 ...
"I loved having a balcony to sit on to view the water. It was perfect for morning coffee or an afternoon to read. The breakfast every morning was perfect, and provided healthy options like fruit and yogurt. I tried a bite of my husband’s omelette and it was excellent. All the staff was friendly and ..."
Reviewed on Nov 12, 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$253 nightly
The price is $285 total per night from Nov 15 to Nov 16
$285 total
Nov 15 - Nov 16
Total with taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...
"Sunrise was beautiful. Loved the private seating out back. Arrived at night and it is not well signed or lit. Bathroom layout with the sink in the bedroom was odd and there was no vanity space to set anything. Menu at the resteraunt was limited. Not all items were available. The value for the money ..."
Reviewed on Nov 10, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$238 nightly
The price is $268 total per night from Nov 16 to Nov 17
$268 total
Nov 16 - Nov 17
Total with taxes and fees
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. ...
"The room was clean and spacious. We stayed in a King suite, garden view. Staff throughout the property were friendly and accommodating. We had breakfast, lunch and dinner at the resort. Food was excellent at the pool and main restaurant. Drinks at the resort were pricey but delicious! Pool areas ..."
Reviewed on Nov 12, 2026
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
$177 nightly
The price is $199 total per night from Nov 18 to Nov 19
$199 total
Nov 18 - Nov 19
Total with taxes and fees
A marina and an outdoor pool are featured at this aparthotel. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
"Rooms werent cleaned daily however the facilities were clean. Beach and pool on-site were excellent"
Reviewed on Nov 9, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $266 total per night from Nov 15 to Nov 16
$266 total
Nov 15 - Nov 16
Total with taxes and fees
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, ...
"The hotel was cute, the room was nice and beds comfy. They need to replace their a few things my refrigerator wasn’t fully closing and the entire bottom was full rust and looked damaged. The bathroom sink has lots of rust. The communication with front end staff and house keeping wasn’t well. I had ..."
Reviewed on Nov 12, 2026
Hadley Resort and Marina
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $200 total per night from Nov 29 to Nov 30
$200 total
Nov 29 - Nov 30
Total with taxes and fees
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 ...
"Good for a single night . We were allowed early check-in at 2pm which was nice. Unfortunately charged with a resort fee in addition to what we have already paid through Hotels.com. Informed at check in that the pool was not operable, but we could use another resort pool down the road ice machine ..."
Reviewed on Nov 12, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $252 total per night from Nov 16 to Nov 17
$252 total
Nov 16 - Nov 17
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
La Jolla Resort
82216 Overseas Highway Islamorada FL
$169 nightly
The price is $190 total per night from Nov 18 to Nov 19
$190 total
Nov 18 - Nov 19
Total with taxes and fees
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 ...
Casa Morada
82200 overseas HWY Islamorada FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Nov 16 to Nov 17
$241 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...
Don't see what you're looking for?
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.
Hotels in Upper Matecumbe Key with star-rating
Check Upper Matecumbe Key Hotels by Star Rating
5 Star Hotels
1 properties
Recent Upper Matecumbe Key hotel reviews by fellow wanderers
Hadley Resort and Marina
4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Good for a single night . We were allowed early check-in at 2pm which was nice. Unfortunately charged with a resort fee in addition to what we have already paid through Hotels.com. Informed at check in that the pool was not operable, but we could use another resort pool down the road ice machine in the building didn’t work, but they were accommodating and gave us a free bag of ice when I asked . Room was very clean, bed was not very comfortable but fine for a night."
A verified traveler stayed at Hadley Resort and Marina
Explore More Ways to Travel with Travelocity
- Hotels near Zoological Wildlife Foundation
- The Hammocks Hotels
- Hotels near The Falls
- Hotels in Tavernier
- Sunset Hotels
- Hotels near Sunset Drive Beach
- Hotels in Sunset Corners
- Hotels near Southland Mall
- Hotels in Conch Key
- Hotels near Coral Reef Park
- Country Walk Hotels
- South Miami Hotels
- Hotels near South Miami Hospital
- South Miami Heights Hotels
- Hotels near South Dade Park
- Hotels near Redland Golf and Country Club
- Hotels in Princeton
- Hotels near Prime Outlets Florida City
- Hotels in Pinecrest
- Hotels near Cutler Ridge Mall
- Hotels near Dagny Johnson Key Largo Hammock Botanical State Park
- Hotels near Dante Fascell Visitor Center
- Hotels near Deering Bay Yacht & Country Club
- Hotels near Deering Estate
- Hotels near The Palms at Town & Country
- Hotels near Ernest F Coe Visitor Center
- Hotels near Everglades National Park
- Hotels near Fairchild Tropical Botanic Garden
- Hotels near Pinecrest Gardens
- Palmetto Estates Hotels
- Palmetto Bay Hotels
- Naranja Hotels
- Hotels near Matheson Hammock Park
- Matecumbe Hotels
- Hotels in Marathon
- Tranquility Bay Beachfront Hotel and Resort
- Isla Bella Beach Resort & Spa
- Hawks Cay Resort
- Lower Matecumbe Beach Hotels
- Hotels near Loren Roberts Park
- Hotels near Long Key State Park
- Hotels in Long Key
- Lime Tree Bay Resort
- Edgewater Lodge
- Hotels near Anhinga Trail
- Hotels near Anne's Beach
- Hotels in Big Pine Key
- Hotels near Biscayne National Park
- Hotels near Boca Chita Key
- Hotels near Bud n' Mary's Dive Center
- Hotels near Camp Owaissa Bauer
- Hotels in Layton
- Resorts in Key Largo
- Hotels in Key Largo
- Marina Del Mar Resort and Marina
- Beach in Key Largo
- Baker's Cay Resort Key Largo Curio Collection by Hilton
- All-Inclusive in Key Largo
- Hotels in Key Colony Beach
- Kendall West Hotels
- Beach in Islamorada
- Breezy Palms Resort
- Cheeca Lodge & Spa
- Chesapeake Beach Resort
- Fisher Inn Resort & Marina
- La Jolla Resort
- La Siesta Resort & Villas
- Pet Friendly in Islamorada
- Pines & Palms Resort
- Hotels in Islamorada
- Resorts in Islamorada
- Hotels near Jimmy Johnson's Big Chill
- Hotels near Kendall Breeze Shopping Center
- Hotels near Kendall Regional Medical Center
- Hotels in Flamingo
- Hotels in Florida City
- Hotels near Florida Keys Dive Center
- Hotels near Founders Park
- Glenvar Heights Hotels
- Goulds Hotels
- Hammocks Hotels
- Hotels near Harry Harris Park
- Hotels near Homestead Air Force Base
- Hotels near Homestead Bayfront Park
- Hotels in Homestead
- Hotels near Homestead Miami Speedway
- Amara Cay Resort
- Hotels near West Kendall District Park
- West Perrine Hotels
- Hotels near Wings Over Miami Museum
- Wynken Blynken and Nod Hotels
- Hotels near Zoo Miami
- Motels in Islamorada
- Flights to Islamorada
- Oceanfront Hotels in Islamorada
- Islamorada vacations
- Islamorada vacation rentals
- Cheap Hotels in Islamorada
- Beach Hotels in Islamorada
- Resorts in Islamorada
- Houseboats in Islamorada
- Pet-friendly Hotels in Islamorada
- Cottages in Islamorada
- Luxury Hotels in Islamorada
- Hotels in Islamorada
