Find hotels in Upper Matecumbe Key, FL from ฿2,525

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24 Jul - 25 Jul
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25 Jul - 26 Jul
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25 Jul - 27 Jul
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1 Aug - 3 Aug

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Top 10 Upper Matecumbe Key hotels and places to stay

Bayside Inn Key Largo
Terrace/patio

Bayside Inn Key Largo

3.0 star property
8.6 out of 10, Excellent, (1542)
"Great location and loved the pier to watch the fireworks! "
The price is ฿3,826
฿5,108 total
includes taxes & fees
7 Aug - 8 Aug
Bayside Inn Key Largo
Chesapeake Beach Resort
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1490)
"Super nice staff! Great place to stay! "
The price is ฿6,078
฿8,647 total
includes taxes & fees
10 Aug - 11 Aug
Chesapeake Beach Resort
Cheeca Lodge & Spa
Private beach, sun-loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1141)
"We absolutely loved our stay at cheeca, will not be our last!"
The price is ฿8,327
฿11,539 total
includes taxes & fees
24 Aug - 25 Aug
Cheeca Lodge & Spa
Rock Reef Resort
Sun deck

Rock Reef Resort

2.5 star property
9.2 out of 10, Wonderful, (1007)
"The staff were very friendly and helpful with all of our questions and gave us amazing recommendations. My family and I absolutely loved our visit here! "
Rock Reef Resort
Sunset Cove Beach Resort
Gazebo

Sunset Cove Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1003)
"My husband and I really enjoyed the private beach and free kayaks! We had the room right on the beach with a gorgeous view of the gulf. We would definitely stay there again. "
The price is ฿5,016
฿5,643 total
includes taxes & fees
17 Aug - 18 Aug
Sunset Cove Beach Resort
Islander Resort
Exterior

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1017)
"Beautiful location loved the rooms and restaurants were excellent "
The price is ฿6,688
฿9,694 total
includes taxes & fees
11 Aug - 12 Aug
Islander Resort
Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1243)
"Amazing stay"
The price is ฿6,246
฿9,160 total
includes taxes & fees
10 Aug - 11 Aug
Amara Cay Resort
La Jolla Resort
View from property

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1003)
"I love staying here! Old Florida charm and convenient to great restaurants!"
La Jolla Resort
Sunset Inn
Outdoor pool, free pool cabanas

Sunset Inn

3.0 star property
9.4 out of 10, Exceptional, (1006)
"The motel, was affordable, clean, and safe."
The price is ฿3,443
฿4,236 total
includes taxes & fees
31 Jul - 1 Aug
Sunset Inn
Islander Bayside Villas and Boatslips
Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (374)
"The villas were nice and relaxing but the association with the islander resort made to stay great. "
The price is ฿7,716
฿10,851 total
includes taxes & fees
17 Aug - 18 Aug
Islander Bayside Villas and Boatslips
Sands of Islamorada
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (386)
"Quiet place which made it a great place to sit and enjoy the view of the water."
The price is ฿5,948
฿7,777 total
includes taxes & fees
10 Aug - 11 Aug
Sands of Islamorada
Pines & Palms Resort
Exterior

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (1001)
"Clean, nice beach and pool area we had a great time. Highly recommend it."
Pines & Palms Resort
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (494)
"Great Property, easy check in and "
The price is ฿2,525
฿4,507 total
includes taxes & fees
17 Aug - 18 Aug
Breezy Palms Resort
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
7.8 out of 10, Good, (1006)
"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 ฿4,022
฿5,574 total
includes taxes & fees
17 Aug - 18 Aug
Hadley Resort and Marina
La Siesta Resort & Villas
Outdoor pool, pool loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1006)
"Pool and bar area very nice and fun for our family "
The price is ฿5,763
฿8,618 total
includes taxes & fees
18 Aug - 19 Aug
La Siesta Resort & Villas
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (63)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ฿17,537
฿21,503 total
includes taxes & fees
1 Aug - 2 Aug
The Islands of Islamorada
Casa Morada
Outdoor pool, pool umbrellas, pool loungers

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (405)
"Charming hotel with beautiful views! "
The price is ฿10,619
฿13,141 total
includes taxes & fees
6 Aug - 7 Aug
Casa Morada
Waterside Suites & Marina
Terrace/patio

Waterside Suites & Marina

3.5 star property
8.8 out of 10, Excellent, (1030)
"I loved it here "
The price is ฿4,551
฿6,024 total
includes taxes & fees
3 Aug - 4 Aug
Waterside Suites & Marina
Drift Hotel
On the beach, sun-loungers, snorkelling, kayaking

Drift Hotel

2.5 star property
9.0 out of 10, Wonderful, (1007)
"Very nice place , good staff"
The price is ฿5,755
฿6,475 total
includes taxes & fees
31 Jul - 1 Aug
Drift Hotel
The Pelican Key Largo Cottages
Marina

The Pelican Key Largo Cottages

2.0 star property
8.6 out of 10, Excellent, (1007)
"Staff was super friendly and place was adorable "
The price is ฿3,120
฿3,510 total
includes taxes & fees
21 Aug - 22 Aug
The Pelican Key Largo Cottages
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:1 Aug - 3 Aug

Image gallery for Islander Bayside Villas and Boatslips

Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
Islamorada
8.8/10Excellent (374 reviews)
10% off
Price is ฿22,744
฿55,515 total
includes taxes & fees
Islander Bayside Villas and Boatslips
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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.

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

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
"Beautiful property "
Rhoden 4-night trip
Posted 3 days ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton