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Check prices for these dates

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17 Aug - 18 Aug
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18 Aug - 19 Aug
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22 Aug - 24 Aug
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29 Aug - 31 Aug

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Top hotels and accommodation in Upper Matecumbe Key

Chesapeake Beach Resort
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1496)
"Great place to stay, safe and quiet"
The price is NZ$376
includes taxes & fees
24 Aug - 25 Aug
Chesapeake Beach Resort
Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1236)
"Very beautiful location"
The price is NZ$431
includes taxes & fees
1 Sept - 2 Sept
Amara Cay 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, (1149)
"Been coming to the keys for 29 years, absolutely the best place we have ever stayed. Staff, rooms, food were second to none. "
The price is NZ$410
includes taxes & fees
21 Aug - 22 Aug
Cheeca Lodge & Spa
La Siesta Resort & Villas
Outdoor pool, pool loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1002)
"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 NZ$390
includes taxes & fees
1 Sept - 2 Sept
La Siesta Resort & Villas
Islander Resort
Exterior

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1003)
" Great location, beautiful hotel!"
The price is NZ$494
includes taxes & fees
24 Aug - 25 Aug
Islander Resort
Sunset Inn
Outdoor pool, free pool cabanas

Sunset Inn

3.0 star property
9.4 out of 10, Exceptional, (1001)
"The motel, was affordable, clean, and safe."
The price is NZ$231
includes taxes & fees
25 Aug - 26 Aug
Sunset Inn
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
7.8 out of 10, Good, (1003)
"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 NZ$259
includes taxes & fees
1 Sept - 2 Sept
Hadley Resort and Marina
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (506)
"Best kept secret, love staying here,!"
The price is NZ$234
includes taxes & fees
7 Sept - 8 Sept
Breezy Palms Resort
Casa Morada
Beach nearby, white sand, sun-loungers, beach umbrellas

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (406)
"The marina was clean and convenient."
The price is NZ$501
includes taxes & fees
21 Aug - 22 Aug
Casa Morada
Pines & Palms Resort
Exterior

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (1000)
"Clean, nice beach and pool area we had a great time. Highly recommend it."
Pines & Palms Resort
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, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is NZ$1,138
includes taxes & fees
18 Aug - 19 Aug
The Islands of Islamorada
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, (387)
"Quiet place which made it a great place to sit and enjoy the view of the water."
The price is NZ$329
includes taxes & fees
7 Sept - 8 Sept
Sands of Islamorada
La Jolla Resort
Private beach, fishing

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!"
La Jolla Resort
Islander Bayside Villas and Boatslips
Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (379)
"The villas were nice and relaxing but the association with the islander resort made to stay great. "
The price is NZ$524
includes taxes & fees
24 Aug - 25 Aug
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Exterior

Coconut Cove Resort and Marina

3.0 star property
7.6 out of 10, Good, (813)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again "
The price is NZ$247
includes taxes & fees
17 Sept - 18 Sept
Coconut Cove Resort and Marina
Hawks Cay Resort
5 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hawks Cay Resort

4.0 star property
8.0 out of 10, Very good, (1006)
"Great stay with family! Lots to do and plenty nearby for other dining and shopping options."
The price is NZ$496
includes taxes & fees
26 Aug - 27 Aug
Hawks Cay Resort
Lime Tree Bay Resort
Exterior

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1089)
"Great place, beautiful apartment! "
Lime Tree Bay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 outdoor pools, a heated pool, pool umbrellas, pool loungers

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

3.5 star property
9.0 out of 10, Wonderful, (57)
"Great resort, excellent staff and customer service, I'll definitely coming back "
The price is NZ$482
includes taxes & fees
1 Sept - 2 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
8.0 out of 10, Very good, (1000)
"Beautiful water and attentive staff."
The price is NZ$276
includes taxes & fees
24 Aug - 25 Aug
Fisher Inn Resort & Marina
Rock Reef Resort
Sundeck

Rock Reef Resort

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Great facility...laid back."
Rock Reef 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:29 Aug - 31 Aug

Image gallery for Islander Bayside Villas and Boatslips

Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
Islamorada
8.8/10Excellent (379 reviews)
9% off
Price is NZ$1,835
NZ$918 nightly
Includes taxes & fees
Islander Bayside Villas and Boatslips
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Learn more about Upper Matecumbe Key

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

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

Top Upper Matecumbe Key Hotel Reviews

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"The place is immaculate. Rooms are very pretty. Breakfast is great. Staff was very helpful. Will definitely be back."
debra 2-night trip
Posted 12 hours ago
Hampton Inn Key Largo Manatee Bay