Find Beach Hotels in Upper Matecumbe Key, FL

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 availability on Upper Matecumbe Key Beach Hotels

Tonight
Nov 3 - Nov 4
Tomorrow
Nov 4 - Nov 5
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top Upper Matecumbe Key Beach Hotels

Private beach, fishing
La Jolla Resort
La Jolla Resort
2.5 star property
  • On private beach
  • Outdoor pool
9.0 out of 10, Wonderful, (1001)
La Jolla Resort
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 star property
  • On private beach
  • Beach loungers
  • 2 outdoor pools
9.2 out of 10, Wonderful, (1553)
This coastal retreat offers marina views plus two refreshing outdoor pools. Beach towels and loungers await, while kayaking, fishing, and boat tours create endless adventures. Nearby snorkeling and jet skiing provide additional thrills on turquoise waters.
The price is ₩175,199
₩277,515 total
includes taxes & fees
Nov 4 - Nov 5
Chesapeake Beach Resort
Exterior
Pines & Palms Resort
Pines & Palms Resort
3.0 star property
  • On private beach
  • Beach bar
  • Beach loungers
  • Outdoor pool
9.2 out of 10, Wonderful, (1008)
This waterfront resort boasts a sandy private beach with complimentary loungers and towels. Adventurous spirits can enjoy snorkeling, kayaking, and parasailing, while those seeking tranquility find solace in beach yoga sessions or refreshing cocktails at the shoreline bar.
Pines & Palms Resort
Exterior
Islander Resort
Islander Resort
4.0 star property
  • On private beach
  • Beach bar
  • Beach cabanas
  • Beach loungers
  • 2 outdoor pools
9.2 out of 10, Wonderful, (1015)
This oceanfront hideaway delights with beach volleyball, kayaking, and paddleboarding right at your doorstep. After exploring turquoise waters, savor beachfront dining, sip refreshing cocktails at the shore bar, then retreat to spacious rooms amid tropical gardens.
The price is ₩297,359
₩431,027 total
includes taxes & fees
Nov 9 - Nov 10
Islander Resort
Exterior
Breezy Palms Resort
Breezy Palms Resort
2.5 star property
  • On the beach
  • Beach towels
  • Outdoor pool
8.8 out of 10, Excellent, (553)
The oceanfront location provides direct beach access with complimentary towels for sun-seekers. Spotlessly clean apartments feature fully equipped kitchens and private balconies. A refreshing pool, marina, and peaceful atmosphere complete this Florida Keys escape.
The price is ₩98,943
₩162,632 total
includes taxes & fees
Nov 11 - Nov 12
Breezy Palms Resort
Alligator Reef Oceanfront Accessible Room King Bed | View from room
Amara Cay Resort
Amara Cay Resort
4.0 star property
  • On private beach
  • Beachfront dining
  • Beach towels
  • Outdoor pool
8.8 out of 10, Excellent, (1277)
The turquoise waters of a private beach beckon at this coastal haven. Adventure seekers can grab kayaks or snorkeling gear before retreating to the outdoor pool with its lively bar. A shuttle whisks guests to nearby excursions while on-site restaurants offer spectacular ocean views.
The price is ₩220,982
₩343,503 total
includes taxes & fees
Nov 30 - Dec 1
Amara Cay Resort
Outdoor pool, sun loungers
La Siesta Resort & Villas
La Siesta Resort & Villas
4.0 star property
  • On private beach
  • Beach towels
  • Outdoor pool
8.6 out of 10, Excellent, (1003)
A coastal haven where sandy shores meet adventure. This resort delivers tranquility with beach access, complimentary towels, and water activities from fishing to kayaking. After exploring nearby hiking trails, unwind by the outdoor pool with a refreshing drink from the pool bar.
The price is ₩211,332
₩332,646 total
includes taxes & fees
Nov 30 - Dec 1
La Siesta Resort & Villas
Restaurant
Bayside Villas by Islander Resort
Bayside Villas by Islander Resort
3.5 star property
  • Near the beach
  • Outdoor pool
8.8 out of 10, Excellent, (392)
This Florida Keys waterfront retreat offers more than just spectacular sunsets. Kayaking, sailing, and motorboating await at the doorstep, while three restaurants satisfy after a day of adventure. A quick 11-minute drive connects guests to pristine beaches.
The price is ₩281,004
₩412,628 total
includes taxes & fees
Nov 20 - Nov 21
Bayside Villas by Islander Resort
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5.0 star property
  • On private beach
  • Beachfront dining
  • Beach loungers
  • 3 outdoor pools
9.2 out of 10, Wonderful, (1268)
This beachside haven offers a complete coastal experience with umbrellas and loungers dotting the private shoreline. Adventurers can enjoy snorkeling, sailing and parasailing, while those seeking tranquility indulge in beach massages and yoga classes.
The price is ₩284,492
₩416,552 total
includes taxes & fees
Nov 4 - Nov 5
Cheeca Lodge & Spa
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio
Sands of Islamorada
Sands of Islamorada
2.5 star property
  • Beach umbrellas
  • Outdoor pool
8.8 out of 10, Excellent, (389)
The morning sun creates a spectacular display over the water at this peaceful Keys retreat. Spacious, well-equipped rooms provide comfort after days spent at the clean outdoor pool or nearby beaches. Guests appreciate the quiet atmosphere and convenient amenities.
The price is ₩213,012
₩258,946 total
includes taxes & fees
Nov 4 - Nov 5
Sands of Islamorada
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.
View all properties

Top Upper Matecumbe Key Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"clean room, great staff "
Dinolis 1-night trip
Posted 20 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Explore a world of travel with Expedia