Photo by Cameron Abbott

Upper Matecumbe Key Hotels

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Our top choices for Upper Matecumbe Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1611)
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 €229
includes taxes & fees
28 Jan - 29 Jan
Chesapeake Beach Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1007)
"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 €402
includes taxes & fees
14 Jan - 15 Jan
Islander Resort

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1281)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is €348
includes taxes & fees
28 Jan - 29 Jan
Cheeca Lodge & Spa

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1271)
"Friendly staff and beautiful property !"
United States
ron
The price is €288
includes taxes & fees
5 Jan - 6 Jan
Amara Cay 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 Centre, 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

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (602)
Immerse yourself in Islamorada with this beachfront aparthotel featuring a marina and outdoor pool. Clean accommodation with kitchens and free WiFi await, while Bud n' Mary's Dive Centre and Hurricane Monument lie nearby.

"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is €182
includes taxes & fees
4 Jan - 5 Jan
Breezy Palms Resort

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1003)
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.

"Good beds, clean room close to Loreleis for sunset dinner. Easy location for Islamorada activities"
United States
Celeste
The price is €149
includes taxes & fees
8 Jan - 9 Jan
Sunset Inn

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1001)
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 Centre and Hurricane Monument, the spacious rooms create an ideal island escape.

"Great accommodations, very peaceful setting "
United States
Susan
The price is €262
includes taxes & fees
8 Jan - 9 Jan
La Siesta Resort & Villas

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

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
8.8 out of 10, Excellent, (404)
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 €368
includes taxes & fees
11 Jan - 12 Jan
Bayside Villas by Islander Resort

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (417)
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 centre.

"always a pleasant stay."
United States
robert
The price is €467
includes taxes & fees
6 Jan - 7 Jan
Casa Morada

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1002)
"Patio nice , pool area good , good walk to things to do ,dive museum , brewery, shopping. "
United States
John
The price is €170
includes taxes & fees
11 Jan - 12 Jan
Hadley Resort and Marina

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70)
Relaxing waterfront villa in Islamorada with pillowtop beds, dressing gowns, 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.

"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is €630
includes taxes & fees
5 Jan - 6 Jan
The Islands of Islamorada

Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (394)
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 Centre.

"The rooms were recently remodeled and very nice. People are really nice."
United States
Tammie
The price is €185
includes taxes & fees
5 Jan - 6 Jan
Sands of Islamorada

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1121)
Escape to this tropical resort with a private beach and complimentary kayaking along Florida's stunning coastline. 3 outdoor pools, tennis courts, and free bike rentals create endless recreation opportunities. Florida Boy restaurant serves American cuisine throughout the day.

"Great sunsets, convenient restaurant next door, great staff."
United States
Kris
Lime Tree Bay Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1077)
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 on-site kayaking or lounge by the outdoor pool. Free WiFi and parking enhance your Keys getaway.

"Cute hotel a great location for our trip through the Keys.. the room was clean and comfortable and the staff was friendly and helpful.. "
United States
Donna
Rock Reef Resort

Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1024)
Discover tropical paradise at this beachfront retreat where 2 outdoor pools and lush gardens create a peaceful oasis. Enjoy snorkelling, diving, and boating right from the marina, plus easy access to local cafes and John Pennekamp Coral Reef State Park.

"Wonderful hotel. Great location Pool is amazing the staff was very friendly In all very good.. highly recommend "
United States
Christopher
The price is €181
includes taxes & fees
4 Jan - 5 Jan
Holiday Inn Key Largo by IHG

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1178)
Overlooking the water in Key Largo, this hotel offers direct marina access for parasailing, diving, and snorkelling adventures. Clean rooms feature private balconies while the outdoor pool provides refreshing relaxation after exploring nearby coral reefs.

"Clean room and staff was great"
United States
Jim
The price is €169
includes taxes & fees
4 Jan - 5 Jan
Waterside Suites & Marina

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1640)
Unwind at this peaceful bayfront retreat with a private beach, kayaks, and paddleboards. Just minutes from John Pennekamp Coral Reef State Park, guests enjoy the outdoor pool, 24-hour fitness centre, and excellent fishing opportunities from the dock.

"Location on the water and restaurant next door made our one night stay on the island fantastic!"
Canada
Csilla
The price is €173
includes taxes & fees
5 Jan - 6 Jan
Bayside Inn Key Largo

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1010)
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.

"Great hotel"
United States
Elior
The price is €126
includes taxes & fees
13 Jan - 14 Jan
Hampton Inn Key Largo Manatee Bay
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

Learn more about Upper Matecumbe Key

Venture to sights like Florida Keys Brewing Co. and Bud n' Mary's Dive Center as you discover 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

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