Find hotels in Upper Matecumbe Key, FL from ₩261,684

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Dec 18 - Dec 19
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Our top choices for Upper Matecumbe Key hotels

Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1597)
Drift into bliss at this tranquil Islamorada oceanfront retreat featuring 2 outdoor pools and a full-service marina. Complimentary breakfast, bike rentals, and spectacular sunset views create an idyllic Florida Keys getaway near diving attractions.
"The entire resort was wonderful."
Canada
Mat
The price is ₩279,198
₩397,169 total
includes taxes & fees
Dec 22 - Dec 23
Chesapeake Beach Resort
House, 3 Bedrooms, Ocean View, Oceanfront | Lanai
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1000)
Experience coastal charm at this oceanside hotel with private beach access. Enjoy the outdoor pool after a day of hiking nearby trails. Convenient to Islamorada Brewery and Keys History Center, with clean rooms and attentive staff to enhance your Florida Keys getaway.
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
La Jolla Resort
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1006)
"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"
United States
Theresa
The price is ₩413,518
₩564,895 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Islander Resort
Outdoor pool, free cabanas
Sunset Inn

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1001)
Explore the Florida Keys from this waterfront hotel with free bikes. The outdoor pool creates a perfect oasis after visiting nearby Islamorada Brewery & Distillery. Friendly staff and complimentary parking enhance the relaxed island experience.
"Room was clean and staff was helpful"
United States
Robert
The price is ₩229,990
₩275,359 total
includes taxes & fees
Dec 21 - Dec 22
Sunset Inn
Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1268)
"Friendly staff and beautiful property !"
United States
ron
The price is ₩347,908
₩489,430 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Amara Cay Resort
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (586)
Immerse yourself in Islamorada with this beachfront aparthotel featuring a marina and outdoor pool. Clean accommodations with kitchens and free WiFi await, while Bud n' Mary's Dive Center and Hurricane Monument lie nearby.
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is ₩164,551
₩261,684 total
includes taxes & fees
Dec 21 - Dec 22
Breezy Palms Resort
Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1270)
"It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!"
United States
Sami
The price is ₩440,846
₩603,775 total
includes taxes & fees
Dec 19 - Dec 20
Cheeca Lodge & Spa
Balcony view
Hadley Resort and Marina

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1000)
"Comfortable stay. Great location. "
United States
Anand
The price is ₩219,637
₩295,282 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hadley Resort and Marina
Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
La Siesta Resort & Villas

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1000)
Experience Florida Keys charm at this beachfront paradise with a private marina. Unwind at the outdoor pool or grab a refreshing cocktail at the poolside bar. Near Bud n' Mary's Dive Center and Hurricane Monument, the spacious rooms create an ideal island escape.
"Great stay and beautiful space"
United States
Amir
The price is ₩308,034
₩444,571 total
includes taxes & fees
Jan 6 - Jan 7, 2026
La Siesta Resort & Villas
Beach umbrellas, beach towels
Sands of Islamorada

Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (392)
Drift away at this waterfront Islamorada retreat offering complimentary WiFi and parking. Unwind in rooms equipped with refrigerators and microwaves, or lounge by the inviting pool. The garden and terrace create a tropical atmosphere near Bud n' Mary's Dive Center.
"The rooms were recently remodeled and very nice. People are really nice."
United States
Tammie
The price is ₩273,217
₩327,314 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sands of Islamorada
Oceanfront Three Bedroom Villa | Premium bedding, individually decorated, individually furnished
Pines & Palms Resort

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1003)
Soak in the Florida Keys atmosphere from this beachfront retreat with its own marina. Relax at the outdoor pool or grab refreshments at the beach bar. Rooms come with refrigerators and microwaves, perfect for enjoying the ocean breeze from your terrace.
"Staff are excellent, resort has been recently upgraded. Best describe his quaint, comfortable and cozy."
Canada
scott
Pines & Palms Resort
Restaurant
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
8.8 out of 10, Excellent, (401)
Located by the ocean, this Islamorada resort offers 3 restaurants and a refreshing outdoor pool. Unwind at the bar/lounge after exploring nearby Hurricane Monument. Free WiFi and parking enhance your Florida Keys escape.
"Beautiful stay!!!"
United States
Lakyne
The price is ₩463,612
₩621,250 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Bayside Villas by Islander Resort
On the beach, sun loungers, beach umbrellas, beach towels
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (69)
Relaxing waterfront villa in Islamorada with pillowtop beds, bathrobes, and premium linens. Swim in 2 outdoor pools, soak in the hot tub, or grab a drink at the pool bar. Near the History of Diving Museum and just 40 minutes from Marathon Airport.
"Great for family vacation with kids. love it"
United States
Dixania
The price is ₩899,402
₩1,093,239 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Islands of Islamorada
Beach nearby, white sand, sun loungers, beach umbrellas
Casa Morada

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (414)
Surrounded by lush gardens on the bay, this Islamorada sanctuary features an outdoor pool with poolside bar. Complimentary bicycles let you explore the area, while deep-tissue massages provide ultimate relaxation. Close to local brewery and discovery center.
"always a pleasant stay."
United States
robert
The price is ₩686,702
₩888,413 total
includes taxes & fees
Dec 23 - Dec 24
Casa Morada
On the beach, sun loungers, snorkeling, kayaking
Drift Hotel

Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1001)
Situated in Key Largo with easy access to Jimmy Johnson's Big Chill, this beach hotel offers complimentary WiFi, parking, bike rentals, and water activities including kayaking and snorkeling. Enjoy the terrace and garden while exploring nearby Pigeon Key.
"Always a great stay"
United States
Ashley
The price is ₩559,726
₩646,308 total
includes taxes & fees
Dec 26 - Dec 27
Drift Hotel
Sundeck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1069)
Relax at this coastal retreat with a private beach just minutes from John Pennekamp Coral Reef State Park. Guests can paddle through scenic waters with onsite kayaking or lounge by the outdoor pool. Free WiFi and parking enhance your Keys getaway.
"Lovely and relaxing waterfront chairs to watch sunset"
United Kingdom
Diana
Rock Reef Resort
Exterior
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina
2.5 star property
Key Largo
8.4 out of 10, Very Good, (1654)
Immerse yourself in stunning marina vistas at this waterfront Key Largo hotel. Relax by the outdoor pool, dine at Bogies Cafe, or explore John Pennekamp Coral Reef State Park nearby. Guests rave about beautiful sunsets and the peaceful atmosphere.
"Great location, amenities, service, places to eat. Very accommodating with extended stay."
United States
Joseph
The price is ₩161,937
₩223,722 total
includes taxes & fees
Dec 21 - Dec 22
Marina Del Mar Resort and Marina
Terrace/patio
Waterside Suites & Marina

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1161)
Overlooking the water in Key Largo, this hotel offers direct marina access for parasailing, diving, and snorkeling adventures. Clean rooms feature private balconies while the outdoor pool provides refreshing relaxation after exploring nearby coral reefs.
"Great place"
United States
Ramon
The price is ₩223,078
₩292,490 total
includes taxes & fees
Dec 20 - Dec 21
Waterside Suites & Marina
Room, 1 King Bed, Bay View | Beach/ocean view
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1009)
Escape to this tranquil Key Largo haven with a private beach offering stunning sunset views. After kayaking adventures, unwind in beautiful gardens surrounding the outdoor pool and enjoy drinks at the bar. Just 5 minutes from coral reef exploration.
"Clean hotel, convenient location. Nice little beach area with tiki bar. Room was nice. "
Canada
Troy
The price is ₩249,351
₩280,520 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Hampton Inn Key Largo Manatee Bay
Exterior
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.6 out of 10, Good, (1001)
Experience Key Largo at this waterfront gem with a marina, outdoor pool, and hot tub. Explore John Pennekamp Coral Reef State Park nearby, or relax in the garden after a day of adventure. Includes free breakfast, WiFi, parking, and bicycles for local exploration.
"The rooms are lovely. Once the remodel is done the place will be perfect. "
United States
Deborah
The price is ₩224,575
₩299,478 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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.
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Stay near popular South Florida attractions

Islamorada_BudnMarysDiveCenter_6069243-0004

Bud n' Mary's Dive Center

4.4/5 (265 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
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Florida Keys Brewing Co. showing signage

Florida Keys Brewing Co.

4.6/5 (152 reviews)
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
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Learn more about Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

See all hotels in Upper Matecumbe Key
Islamorada Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.
Photo by Cameron Abbott
Open Photo by Cameron Abbott

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"The entire resort was wonderful."
Mat 3-night trip
Posted 1 day ago
Chesapeake Beach Resort

More cheap stays in Upper Matecumbe Key

Breezy Palms Resort

Breezy Palms Resort

80015 Overseas Highway Islamorada FL
The price is ₩164,551 per night from Dec 21 to Dec 22
₩164,551
₩261,684 total
Dec 21 - Dec 22
includes taxes & fees
8.8/10 Excellent! (586 reviews)