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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Villas in Upper Matecumbe Key

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 AU$1,036
includes taxes & fees
19 Aug - 20 Aug
The Islands of Islamorada
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
A heated pool

Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

The price is AU$4,274
includes taxes & fees
19 Aug - 20 Aug
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
Villa 5027 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (54)
"Very clean. "
The price is AU$882
includes taxes & fees
19 Aug - 20 Aug
Villa 5027 on Duck Key BOAT SLIP available
Villa 5086 on Duck Key
Exterior

Villa 5086 on Duck Key

8.6 out of 10, Excellent, (25)
"Host answered all questions promptly and is very professional "
The price is AU$863
includes taxes & fees
19 Aug - 20 Aug
Villa 5086 on Duck Key
Villa 7075 on Duck Key BOAT SLIP available
Property grounds

Villa 7075 on Duck Key BOAT SLIP available

9.2 out of 10, Wonderful, (29)
"Great location, incredible view just as advertised. Definitely would stay there again."
Villa 7075 on Duck Key BOAT SLIP available
Villa 5087 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5087 on Duck Key BOAT SLIP available

9.2 out of 10, Wonderful, (18)
"Frank made the whole process easy and he has excellent properties that are A on the clean scale!"
The price is AU$924
includes taxes & fees
31 Aug - 1 Sept
Villa 5087 on Duck Key BOAT SLIP available
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Exterior

Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay."
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available
Terrace/patio

Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available

The price is AU$1,738
includes taxes & fees
19 Aug - 20 Aug
Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available
Villa 5034 on Duck Key Boat Slip available
Exterior

Villa 5034 on Duck Key Boat Slip available

10.0 out of 10, Exceptional, (4)
"Everything about the stay was nice. "
The price is AU$902
includes taxes & fees
21 Aug - 22 Aug
Villa 5034 on Duck Key Boat Slip available
Villa 5028 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5028 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (7)
"Great location on the water with beautiful sunset views. Plenty of room for our group. "
The price is AU$885
includes taxes & fees
31 Aug - 1 Sept
Villa 5028 on Duck Key BOAT SLIP available
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.
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Top Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Property newly renovated, felt fresh and new. Beds and pillows were comfortable. We made use of the courtesy shuttle to get to some local bars and restaurants. Pool area was great, lots of chairs and towels readily available. Water temperature was perfect. "
stephanie 1-night trip
Posted 21 hours ago
Islander Resort