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Featured Condo Rentals in Upper Matecumbe Key

Paradise Awaits: 2 BR Beautiful Condo w/ Pool, Beach, Marina & Resort Perks

10.0 out of 10, Exceptional, (69)
"Location and property grounds were great. The pool area was large and very clean and the pool bar was a nice touch! The condo was good overall but could use a deep clean and some minor updates. I would recommend Ocean Pointe suites for families. "
Paradise Awaits: 2 BR Beautiful Condo w/ Pool, Beach, Marina & Resort Perks

Its an enjoyable two bed/bath unit with pleasant view of the marina and 0cean.

8.8 out of 10, Excellent, (136)
"We had a great week! The condo was clean, comfortable beds, nice view, loved the gated community. Francisco was a great host! Super friendly, very helpful. I would definitely stay here again recommend his place highly!"
Its an enjoyable two bed/bath unit with pleasant view of the marina and 0cean.

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (168)
"Clean, short walk to the beach or pool. Great place to stay."
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

9.6 out of 10, Exceptional, (41)
"Loved the property, location and amenities! The condo was exactly as advertised. "
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

Ocean View Suite, Top Floor, Updated

10.0 out of 10, Exceptional, (69)
"Property consists of 5 buildings 250 units. This unit was very clean and well appointed with everything you need for a comfortable stay. The pool was large, clean and a popular area. Seating in the pool area could use an upgrade. We enjoyed the serene beach area over by the marina. Enjoyed the Islamorada area for dining which is the next town so close by. Overall enjoyed our time!"
Ocean View Suite, Top Floor, Updated

Mariners Club 316 Oceanfront Condo, Epic Amenities, Pickleball

10.0 out of 10, Exceptional, (23)
"Our families had such a great time staying here! Beautiful property, well stocked with the essentials and communication was excellent! We would definitely stay again!"
Mariners Club 316 Oceanfront Condo, Epic Amenities, Pickleball

Condo with Pool and Beach Access

10.0 out of 10, Exceptional, (9)
"This was our second time at Ocean Pointe Suites and our time in this condo. The condo was perfect for our family. "
Condo with Pool and Beach Access

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

9.8 out of 10, Exceptional, (206)
"The condo is right on the water at a marina! There were several options for great food or you could go to the store and cook in house. The pool was a great relief from the surprisingly warm weather! Great amenities as well and the King bed was very comfortable!"
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Breathtaking Waterfront Key Largo Boat Slip, Oasis

10.0 out of 10, Exceptional, (17)
"This location was perfect for brining our boat down. Great little unit that fit all of our needs, super clean, excellent bed and kitchen was functional. "
Breathtaking Waterfront Key Largo Boat Slip, Oasis

Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina & more....

10.0 out of 10, Exceptional, (245)
"All good! Back deck only fit 1 person at a time and we all love sitting out so that was down fall! "
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina & more....

Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys

9.8 out of 10, Exceptional, (147)
"Great place to stay! Beautiful condo and gorgeous views. "
Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys

Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!

9.8 out of 10, Exceptional, (43)
"This unit is located within 5 minutes of so many things. From restaurants, to the fish company, to gift shops, to Diver’s Direct, you are close. The unit is big and beds are comfortable. The washer & dryer work well but you’ll have to wash dishes by hand. The view over the boars is relaxing."
Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!

Stay on the Atlantics Edge, Marina & Ocean Front Suite [ Ocean Pointe 5202]

9.6 out of 10, Exceptional, (96)
"Overall a nice condo in a good central location in Tavernier, which is an easy 20min drive to Key Largo or Islamorada, or a 2hr drive to Key West. Check-in was easy and the automated gate access via license plate worked well. The beach/boardwalk area is small but nice, but recommend water shoes if you want to swim. The pool area gets crowded quickly, as people come out to claim chairs soon after opening. The other negative is they don't allow outside food or drink in favor of a pricey onsite...
Stay on the Atlantics Edge, Marina & Ocean Front Suite [ Ocean Pointe 5202]

Welcome to Paradise!

9.6 out of 10, Exceptional, (60)
"We were there for a destination wedding. The room and property were everything we’d hoped for. Met a number of other guests and had a great time getting to know each other. Overall it was a wonderful experience and the condo was great!"
Welcome to Paradise!

Water Front Condo in Duck Key. FREE WIFI/CABLE. Over looking Gulf of Mexico.

9.6 out of 10, Exceptional, (37)
"Three single women enjoyed the condo. Nice to have an elevator to go up three floors. Three bedrooms meant that we each had our privacy. The spacious lanai was super with a nice space for meals and conversation. Nice property for walking or biking. Convenient location to Marathon, where we found some interesting activities - Dolphin Research Center, Crane Point Hammock, and the Turtle Hospital. All three had very interesting guided tours. We enjoyed a day trip in Key West - 1.5 hours drive...
Water Front Condo in Duck Key. FREE WIFI/CABLE. Over looking Gulf of Mexico.

Overlooking The Marina and Ocean Includes Use of Golf Cart Pet-Friendly

10.0 out of 10, Exceptional, (21)
"Very nice condo in a great location. Host was excellent to work with. "
Overlooking The Marina and Ocean Includes Use of Golf Cart Pet-Friendly

Duck Key Getaway: Charming 3BR Condo with Water Views, Steps from Angler & Ale, Near Marathon

8.4 out of 10, Very good, (35)
"We had an amazing time but the sink in master did not drain, the faucets were reversed hot/cold the shampoo dispenser did not work very limited in glasses and drinking cups. Didn't include coffee or any other stocked items. The location was perfect and the home was very cozy and convenient. Thank you."
Duck Key Getaway: Charming 3BR Condo with Water Views, Steps from Angler & Ale, Near Marathon

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

9.6 out of 10, Exceptional, (188)
"We loved our stay at this property!! Great communication with the owner and a good location to make some day trips to different parts of the keys. The kitchen was stocked with all of the dishes and cookware we needed. We didn't spend any time by the pool or on the beach, but those areas looked nice as well. Would definitely recommend staying here."
The price is AU$700
includes taxes & fees
13 Mar - 14 Mar
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Toes in the Sand - 2 Bedroom Condo Sleeps 4

10.0 out of 10, Exceptional, (20)
"Very comfortable condo with everything we needed. Secure property. Beautiful huge pool and nice hot tub. The beach bar and restaurant were convenient. Relaxing view over a nature area with the ocean beyond. "
The price is AU$959
includes taxes & fees
28 Mar - 29 Mar
Toes in the Sand - 2 Bedroom Condo Sleeps 4

Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball

9.8 out of 10, Exceptional, (24)
"Great place very clean. The place was very modern. Loved it. Loved the deck and the view of the boats and the water. Pool was heated felt great. RestaurantRestaurants "
Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball
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, (421)
"We visited Breezy Palms for our 20th wedding anniversary. We took advantage of the boat rental on site, had a great day on the water. Played cards on our lanai. Used the lovely pool, walked to local restaurants, and had a memorable time. Definitely will be back!"
The price is AU$360
includes taxes & fees
6 Apr - 7 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is AU$1,121
includes taxes & fees
6 Apr - 7 Apr
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.