Upper Matecumbe Key Private Home Rentals

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Check prices for these dates

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

Featured Private Holiday 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 S$616
includes taxes & fees
4 Feb - 5 Feb
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 S$595
includes taxes & fees
3 Feb - 4 Feb
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 resort was beautiful, clean, and well managed. We had a beautiful room with stylish furniture. Fun things to do at the resort (fish, swim, pitch and putt golf), within walking distance to other fun restaurants and stores. "
The price is S$701
includes taxes & fees
6 Feb - 7 Feb
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, (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 S$547
includes taxes & fees
4 Feb - 5 Feb
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 S$584
includes taxes & fees
9 Feb - 10 Feb
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 S$366
includes taxes & fees
3 Feb - 4 Feb
Hadley Resort and Marina
Sunset Inn
Outdoor pool, free pool cabanas

Sunset Inn

3.0 star property
9.2 out of 10, Wonderful, (1003)
"Highly recommend "
The price is S$357
includes taxes & fees
3 Feb - 4 Feb
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 S$342
includes taxes & fees
3 Feb - 4 Feb
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, pool 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 S$540
includes taxes & fees
9 Feb - 10 Feb
Islander Bayside Villas and Boatslips
Casa Morada
Outdoor pool, pool umbrellas, pool 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 S$559
includes taxes & fees
3 Feb - 4 Feb
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 S$411
includes taxes & fees
9 Feb - 10 Feb
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 S$470
includes taxes & fees
3 Feb - 4 Feb
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)
"The pictures online do not do this place justice. Tucked between two larger hotels, it’s like an oasis. Our room in particular had a grassy lawn facing the water, was spotless and well appointed. Small beach, pool and sandy area (volleyball court) is adjacent to a dock and boat launch for interesting views. Lots of iguanas and a local rooster completes the ambiance. "
The price is S$293
includes taxes & fees
13 Feb - 14 Feb
Breezy 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, (47)
"Beautiful property with great staff! "
The price is S$982
includes taxes & fees
2 Mar - 3 Mar
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 S$638
includes taxes & fees
9 Feb - 10 Feb
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.