Search Upper Matecumbe Key Villa Rentals from CA $372

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Browse Select Upper Matecumbe Key Villas

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (57)
"Such a beautiful, quiet and clean location. The staff were attentive and helpful. "
The price is CA $737
CA $906 total
includes taxes & fees
May 11 - May 12
The Islands of Islamorada

Sea Haven with Resort Privileges

9.6 out of 10, Exceptional, (4)
"Highly recommend!"
Sea Haven with Resort Privileges

Gull's Nest with Resort Privileges

9.6 out of 10, Exceptional, (21)
"The property manager was absolutely amazing. We had an issue getting down to the keys due to the wildfires and she was available to talk to us and help us any moment we asked a question. The property was very clean and the grounds and amenities were great. "
Gull's Nest with Resort Privileges

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (49)
"Very clean. "
The price is CA $372
CA $833 total
includes taxes & fees
May 5 - May 6
Villa 5027 on Duck Key BOAT SLIP available

Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

8.8 out of 10, Excellent, (227)
"Good overall. Master bathroom had slight issues with toilet and shower."
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

Endless Summer with Resort Privileges

9.4 out of 10, Exceptional, (12)
"We had a lovely weekend staying on the property. It was spacious and convenient a very nice facility and access to the resort made it outstanding. It was very easy to order groceries for delivery, which were there waiting for us when we arrived. I definitely recommend this property for anyone with a larger group or family. I do suggest that the management let guests know the number of the unit they are renting just to facility logistics like ordering groceries. However, I was easily able to find...
Endless Summer with Resort Privileges

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

9.8 out of 10, Exceptional, (149)
"Overall, the rental was good. Nice area for morning walks. It’s a smaller place and is full of furniture, which makes it feel a bit cramped in the living area. Beds were comfortable and bathroom updates were nice. Outdoor space is nice but furniture is looking tired and ready for updates. The pool is lovely. Luckily for us, the neighbors were never there. So, we had it all to ourselves. "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

✦Unwind on your Oceanedge villa on Seapalm island✦

9.8 out of 10, Exceptional, (31)
"Great house. Nice amenities- peaceful and secluded. However no beach access from house. Nearest beach is Sombrero beach which is very nice."
✦Unwind on your Oceanedge villa on Seapalm island✦

Villages at Hawks Cay Villa with Spa

10.0 out of 10, Exceptional, (208)
"First time we have been able to return to a property and we were glad we could stay again.This is a clean, well appointed property in the mid Key area. It has two bedrooms and 2.5 bathrooms. The downstairs half bath was appreciated. It's in a nice area with views of the canal. It has a jacuzzi in the backyard.Grocery store and most of the restaurants we went to were in Marathon.All 4 of us , were very happy to return and would love to stay again."
Villages at Hawks Cay Villa with Spa

DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

10.0 out of 10, Exceptional, (160)
"The condo was very clean and comfortable. The outside tiki sitting area was the bomb. "
DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

Sandcastle Luxury Villa in Key Largo with Resort Privileges

10.0 out of 10, Exceptional, (2)
"The house was gorgeous and we would definitely recommend it to everyone."
Sandcastle Luxury Villa in Key Largo with Resort Privileges

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

9.8 out of 10, Exceptional, (61)
"The town house was nice, clean, quiet. Good location close to marathon "
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

9.6 out of 10, Exceptional, (64)
"Our unit was super clean and met all of our needs We enjoyed how big the place was and the overall property had plenty for us to do! Great location too"
The price is CA $623
CA $1,257 total
includes taxes & fees
Apr 22 - Apr 23
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

10.0 out of 10, Exceptional, (187)
"We had a great time exploring the keys"
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

Villa 5034 on Duck Key Boat Slip available

10.0 out of 10, Exceptional, (3)
"No complaints about this listing. We had a great time cruising up and down the keys. I love the porch and balcony to hang out and watch the sunsets. Only thing I wish they had were board games. "
The price is CA $400
CA $892 total
includes taxes & fees
May 5 - May 6
Villa 5034 on Duck Key Boat Slip available

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

10.0 out of 10, Exceptional, (111)
"Celebration of my Husbands 70th perfect "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Twilight with Resort Privileges

10.0 out of 10, Exceptional, (1)
"What a great option to have access to the hotel but come back each day and finish at the clubhouse pool for sunset! Really great house with plenty of room and great variety to get away from the hotel! "
Twilight with Resort Privileges

Stunning Waterfront Two-Story Villa in Duck Key!

2.0 star property
10.0 out of 10, Exceptional, (3)
"As listed, great views, and property is well kept. "
Stunning Waterfront Two-Story Villa in Duck Key!

Waterfront Duck Key Villa

9.4 out of 10, Exceptional, (59)
"Our group of 8 really enjoyed this property. We found it very clean and the back porch on the water was loved by all!!!"
The price is CA $829
CA $1,577 total
includes taxes & fees
Apr 23 - Apr 24
Waterfront Duck Key Villa

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

8.6 out of 10, Excellent, (47)
"Was clean and comfortable. Only mirrors are in the bathroom with very little vanity space. They answered every call. Blinds moved very hard or didn’t. Very enjoyable stay. Loved sitting on the deck."
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
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

2.5 star property
8.6 out of 10, Excellent, (450)
"We enjoyed our stay. Balcony room overlooking the marina was great. Walked to restaurant nearby. Would stay again."
The price is CA $170
CA $213 total
includes taxes & fees
Apr 27 - Apr 28
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (57)
"Such a beautiful, quiet and clean location. The staff were attentive and helpful. "
The price is CA $737
CA $906 total
includes taxes & fees
May 11 - May 12
The Islands of Islamorada

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."
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.