A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Find all hotels by Aimbridge Hospitality in Upper Matecumbe Key, FL

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 27 - Aug 28
Tomorrow
Aug 28 - Aug 29
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6
Save an average of 15% on thousands of hotels when you're signed in

Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"We arrived one hour and twenty minutes before check in and were told there were no available rooms, although I am positive there were clean ready rooms. My husband and I went to the pool and enjoyed some music before checking into our room. Room was clean and comfortable. Continental breakfast served the next morning. The attendance were lovely and seemed happy to be at work. Check out soon after."
Cheryl 1-night trip
Posted less than an hour ago
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Everything was great but the breakfast wasn’t that great and sometimes no one would wait on you but we went out to eat anyway. Bartender was amazing!!"
Deirdre 4-night trip
Posted 10 hours ago
Amara Cay Resort
Casa Morada

Casa Morada

8/10 Good
"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."
Jeremy 1-night trip
Posted 12 hours ago
Casa Morada
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"The property was situated to make you feel like you were in a tropical paradise tucked away from the rest of the key. Very clean and nice. The staff was amazing and the private beach was one of the best."
Preston 2-night trip
Posted 12 hours ago
Playa Largo Resort & Spa, Autograph Collection
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"I was really enjoying my time at Hawks Cay Resort. The views here were absolutely breathtaking! 🌴🌊😍 I just wanted to relax, enjoy the beautiful scenery, and make the most of every moment of my vacation."
XianS 1-night trip
Posted 19 hours ago
Hawks Cay Resort
Breezy Palms Resort

Breezy Palms Resort

8/10 Good
"The room was spacious and clean. We were very happy with it. They only provide maid service every 3 days, and that was simply changing sheets and towels. The only issue is the smell from the beach due to dead sea grass and other stink. It made the beach impossible to use, and often was unpleasant anytime you went outside. If you plan to use the private beach, this hotel is not for you."
Sherrill 5-night trip
Posted 2 days ago
Breezy Palms Resort
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Clean room and staff"
Steve 3-night trip
Posted 2 days ago
Waterside Suites & Marina
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Excellent place to stay!"
Jose 3-night trip
Posted 2 days ago
The Caribbean Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Great spot for a vacation quiet clean spacious on the go breakfast. Also the ability to rent the boat while you’re there is also awesome. I would definitely reserve one beforehand. Other than that will be back again. I highly recommend this place."
Jaimie 3-night trip
Posted 3 days ago
Hadley Resort and Marina

Explore a world of travel with Expedia