Search Vacation Homes in Upper Matecumbe Key

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Featured Vacation Homes in Upper Matecumbe Key

Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1216)
"Reception desk staff accommodated our early arrival by giving us access to the hotel grounds and contacted us when our room was ready. Lobby, reception and grounds were very well maintained and all staff encountered is personable and engaging. "
The price is P20,094
P26,481 total
includes taxes & fees
Feb 4 - Feb 5
Amara Cay Resort
Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1393)
"Went to a weeding in Islamorada and the option of the hotel was ideal "
The price is P16,869
P25,590 total
includes taxes & fees
Feb 3 - Feb 4
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, (1033)
"The staff"
The price is P23,290
P30,141 total
includes taxes & fees
Feb 6 - Feb 7
Cheeca Lodge & Spa
La Siesta Resort & Villas
Outdoor pool, sun loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1004)
"It’s very relaxing with tropical feel. It feels like a private quiet island. Noel at the tiki bar was great. "
The price is P17,468
P23,526 total
includes taxes & fees
Feb 5 - Feb 6
La Siesta Resort & Villas
Islander Resort
Exterior

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1009)
"Great property and service!!! View is amazing!!!"
The price is P19,098
P25,162 total
includes taxes & fees
Feb 9 - Feb 10
Islander Resort
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
8.0 out of 10, Very Good, (1002)
"When we arrived our room was ready and the staff was very friendley."
The price is P12,293
P15,734 total
includes taxes & fees
Feb 3 - Feb 4
Hadley Resort and Marina
Sunset Inn
Outdoor pool, free cabanas

Sunset Inn

3.0 star property
9.2 out of 10, Wonderful, (1003)
"Outstanding. Friendly staff. Simple, spacious, immaculately clean room. Grounds were well kept and the pool warm and deck area inviting. Absolutely will be back."
The price is P13,081
P15,373 total
includes taxes & fees
Feb 3 - Feb 4
Sunset Inn
La Jolla Resort
View from property

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Friendly and helpful staff. Nice room"
The price is P11,616
P14,710 total
includes taxes & fees
Feb 3 - Feb 4
La Jolla Resort
The Caribbean Resort
Exterior

The Caribbean Resort

3.5 star property
10.0 out of 10, Exceptional, (150)
"Staff is always great. Rooms are beautiful & clean. Feels like I am at home"
The Caribbean Resort
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (358)
"We booked here because of the full kitchen plus living areas; the kitchen was pretty sparse regarding cookware/appliances, but the front desk bent over backwards to get us the missing items we requested. One of the selling points was access to their resort property, just up the street. However, that property was almost deserted due to a lot of construction work. The resort pool was closed (the Bayside Villas pool was open). Overall this was a pleasant stay for us."
The price is P19,098
P25,162 total
includes taxes & fees
Feb 9 - Feb 10
Islander Bayside Villas and Boatslips
Casa Morada
Outdoor pool, pool umbrellas, sun loungers

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (378)
"Stayed overnight while attending a wedding on Islamorada. Room was comfortable and the property was beautiful! Wish we were able to stay for more than one night. Was pleasantly surprised to learn of the morning yoga class on Sunday mornings! Felt great to stretch and practice mindfulness. Will definitely stay at Casa Morada again in the future!"
The price is P17,657
P24,242 total
includes taxes & fees
Feb 3 - Feb 4
Casa Morada
Sands of Islamorada
Terrace/patio

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (355)
"Loved the location of our room-we could easily get coffee and head out to sit and watch the sunrise. Ice machine broken so that was a bummer but the staff was phenomenal especially when allowing us to check in early."
The price is P13,951
P17,665 total
includes taxes & fees
Feb 9 - Feb 10
Sands of Islamorada
Pines & Palms Resort
Poolside bar

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (975)
"Place was under heavy construction, when booking stay know one mentioned the whole resort is under reconstruction. Besides the construction the location was beautiful setting "
The price is P13,951
P20,226 total
includes taxes & fees
Feb 3 - Feb 4
Pines & Palms 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.
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Other property types in Upper Matecumbe Key

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (403)
"Great location Nice beach Friendly staff Walking distance to restaurants"
The price is P10,388
P12,617 total
includes taxes & fees
Feb 13 - Feb 14
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (47)
"Beautiful property with great staff! "
The price is P34,681
P42,234 total
includes taxes & fees
Mar 2 - Mar 3
The Islands of Islamorada
Key Largo Cottages
Beach/ocean view

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is P18,095
P29,076 total
includes taxes & fees
Feb 5 - Feb 6
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.