Find hotels in Upper Matecumbe Key, FL from ₩115,118

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 3 - Aug 4
Tomorrow
Aug 4 - Aug 5
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Filter by

Guest rating
Guest rating
Star rating

Compare 2,765 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Chesapeake Beach Resort
Relax on the beach with a tranquil ocean view and comfortable sun loungers.

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1488)
"The hotel is wonderful "
The price is ₩209,879
₩314,270 total
includes taxes & fees
Aug 10 - Aug 11
Chesapeake Beach Resort
Amara Cay Resort
Relax in a serene outdoor seating area with Adirondack chairs around a central fire pit, surrounded by palm trees and ocean views.

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1237)
"Great hotel a family room "
The price is ₩233,536
₩354,961 total
includes taxes & fees
Sep 1 - Sep 2
Amara Cay Resort
Cheeca Lodge & Spa
Relax on the beach with lounge chairs, a shaded hut, and a long pier extending into the calm sea.

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1144)
"Great chill location. "
The price is ₩276,505
₩404,864 total
includes taxes & fees
Aug 13 - Aug 14
Cheeca Lodge & Spa
La Siesta Resort & Villas
Relax by the uniquely shaped pool surrounded by palm trees and shaded by umbrellas.

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1003)
"Fantastic staff working there. Incredibly friendly and helpful. Very clean rooms and loved being able to take the water taxi to the 2 other resorts "
The price is ₩205,398
₩323,306 total
includes taxes & fees
Sep 1 - Sep 2
La Siesta Resort & Villas
Islander Resort
Relax in comfort on the beach with lounge chairs and enjoy the ocean views.

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1010)
"Beautiful location loved the rooms and restaurants were excellent "
The price is ₩289,010
₩418,924 total
includes taxes & fees
Aug 11 - Aug 12
Islander Resort
Sunset Inn
Relax by the pool surrounded by palm trees and lounge chairs, with umbrellas providing shade.

Sunset Inn

3.0 star property
9.4 out of 10, Exceptional, (1000)
"The motel, was affordable, clean, and safe."
The price is ₩166,647
₩203,110 total
includes taxes & fees
Aug 26 - Aug 27
Sunset Inn
Hadley Resort and Marina
Enjoy waterfront views and access to boat rentals and guided tours from this serene dock.

Hadley Resort and Marina

3.5 star property
7.8 out of 10, Good, (1002)
"We stayed in the “Villas” on our 2nd stay and it was comfortable at a very affordable price. This is an older hotel and villa we had was clean and the furniture was in good condition. "
The price is ₩173,822
₩240,888 total
includes taxes & fees
Aug 17 - Aug 18
Hadley Resort and Marina
Breezy Palms Resort
Relax on the beachfront lawn with lounge chairs, enjoy the tranquil atmosphere, and take in the views of the calm sea.

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (500)
"Excellent room and staffs!!!!!"
The price is ₩115,118
₩201,543 total
includes taxes & fees
Aug 19 - Aug 20
Breezy Palms Resort
Casa Morada
Relax on the beach with ocean views, sun loungers, and shade from umbrellas.

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (406)
"Charming hotel with beautiful views! "
The price is ₩440,184
₩544,728 total
includes taxes & fees
Aug 7 - Aug 8
Casa Morada
Pines & Palms Resort
Relax on the beach with a clear view of the ocean from a wooden pier, surrounded by palm trees and comfortable lounge chairs.

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (1000)
"Wonderful stay. Amazing desk staff upon arrival. "
The price is ₩223,843
₩328,424 total
includes taxes & fees
Aug 17 - Aug 18
Pines & Palms Resort
The Islands of Islamorada
Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (65)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ₩757,255
₩928,505 total
includes taxes & fees
Aug 6 - Aug 7
The Islands of Islamorada
Sands of Islamorada
Enjoy the serene ocean views from this expansive deck, surrounded by palm trees and overlooking the sandy beach.

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (387)
"Quiet place which made it a great place to sit and enjoy the view of the water."
The price is ₩225,094
₩300,126 total
includes taxes & fees
Aug 5 - Aug 6
Sands of Islamorada
La Jolla Resort
Relax on the beach with lounge chairs and umbrellas at La Jolla Resort.

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1001)
"I love staying here! Old Florida charm and convenient to great restaurants!"
The price is ₩136,307
₩192,432 total
includes taxes & fees
Aug 14 - Aug 15
La Jolla Resort
Islander Bayside Villas and Boatslips
Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (378)
"The villas were nice and relaxing but the association with the islander resort made to stay great. "
The price is ₩299,125
₩430,305 total
includes taxes & fees
Sep 1 - Sep 2
Islander Bayside Villas and Boatslips
Hawks Cay Resort
Relax by the pool surrounded by palm trees and lounge chairs.

Hawks Cay Resort

4.0 star property
8.0 out of 10, Very Good, (1010)
"Great stay with family! Lots to do and plenty nearby for other dining and shopping options."
The price is ₩398,778
₩545,721 total
includes taxes & fees
Aug 22 - Aug 23
Hawks Cay Resort
Coconut Cove Resort and Marina
Exterior

Coconut Cove Resort and Marina

3.0 star property
7.6 out of 10, Good, (810)
"Really liked the property and staff was very informative and kind. Also love the 24 hour pool access!"
The price is ₩198,833
₩223,688 total
includes taxes & fees
Sep 2 - Sep 3
Coconut Cove Resort and Marina
Lime Tree Bay Resort
Relax by the clear swimming pool surrounded by lounge chairs and umbrellas, with access to the beach and shallow waters.

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1089)
"It was a lovely property. Comfortable beds & clean."
The price is ₩181,145
₩266,320 total
includes taxes & fees
Aug 17 - Aug 18
Lime Tree Bay Resort
Bayside Inn Key Largo
Relax by the oceanfront pool surrounded by palm trees and lounge under the shade of an umbrella.

Bayside Inn Key Largo

3.0 star property
8.6 out of 10, Excellent, (1547)
"Great location and loved the pier to watch the fireworks! "
The price is ₩163,957
₩219,188 total
includes taxes & fees
Aug 24 - Aug 25
Bayside Inn Key Largo
Fisher Inn Resort & Marina
Relax by the pool or on the beach, with lounge chairs and a dock leading into the ocean.

Fisher Inn Resort & Marina

3.5 star property
8.0 out of 10, Very Good, (1002)
"For the price, it is great to spend a weekend and enjoy the Islamorada sandbar."
The price is ₩158,400
₩223,537 total
includes taxes & fees
Aug 12 - Aug 13
Fisher Inn Resort & Marina
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
9.0 out of 10, Wonderful, (53)
"This place is a gem. It was beautiful and quiet. "
The price is ₩246,839
₩369,927 total
includes taxes & fees
Aug 19 - Aug 20
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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.

Great weekend hotel deals in Upper Matecumbe Key, FL

Showing deals for:Aug 15 - Aug 17

Image gallery for Islander Bayside Villas and Boatslips

Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
Islamorada
8.8/10Excellent (378 reviews)
10% off
Price is ₩510,714
₩1,336,683 total
includes taxes & fees
Islander Bayside Villas and Boatslips
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Upper Matecumbe Key

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

See all hotels in Upper Matecumbe Key
Islamorada showing a beach bar

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Breakfast selections were very good, including made to order omelettes and waffles. Loved the 2 pools, free beach chairs, umbrellas, towels, kayaks. Beach and water had tons of sea weed but staff did best to keep paths open. Beautiful setting, well kept"
David 2-night trip
Posted 12 hours ago
Chesapeake Beach Resort