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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Condo Rentals in Upper Matecumbe Key

Our top choices for Upper Matecumbe Key condo rentals

Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (268)
"We enjoyed our stay! It was a great condo and was exactly as described in the listing. "
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina and more....
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Outdoor pool, a heated pool

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

9.6 out of 10, Exceptional, (55)
"This condo exceeded our expectations! It was immaculately clean and had a cozy, welcoming feel. The view was spectacular, offering a serene and beautiful backdrop. We had everything we needed, from kitchen essentials to comfy furniture, making our stay seamless and enjoyable. It’s the perfect spot for a relaxing escape. Highly recommend!"
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (221)
"Condo was clean and quiet. Loved the main suite in the back."
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Smart TV, fireplace

Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

9.6 out of 10, Exceptional, (56)
"Lovely location; lovely setting."
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
On the beach, sun-loungers, beach towels

Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities

10.0 out of 10, Exceptional, (13)
"We had an amazing stay at this Key Largo condo! The location is ideal—very central to everything in the area. One of the highlights was having access to a golf cart, which made it easy and fun to explore the neighborhood and surrounding areas on local roads.The condo itself was clean, comfortable, and well-equipped. The beds were cozy, there were plenty of fresh towels, and the kitchen had all the essentials we needed. Each room had a smart TV, which was a great bonus for relaxing in the...
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
Welcome to Paradise!
Beach nearby, sun-loungers, beach towels

Welcome to Paradise!

9.6 out of 10, Exceptional, (72)
"This one bedroom is in the Tower of Kawama a great central location on Key Largo. We enjoyed the ocean view as well as the pool area. We would certainly stay again. "
Welcome to Paradise!
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Marina

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

9.8 out of 10, Exceptional, (186)
"Nice place, lots to do, great location, great views"
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
SeaGulls, Panoramic Ocean Views, Corner Condo, POOL, WiFi, Covered Parking, Gym
On the beach, sun-loungers, beach towels

SeaGulls, Panoramic Ocean Views, Corner Condo, POOL, WiFi, Covered Parking, Gym

9.8 out of 10, Exceptional, (168)
"Idea location, the best view you could’ve asked for and so clean "
SeaGulls, Panoramic Ocean Views, Corner Condo, POOL, WiFi, Covered Parking, Gym
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Marina

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

10.0 out of 10, Exceptional, (173)
"Very nice, close to the pool, nice amenities, close to tons of great food options."
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Outdoor pool, a heated pool

Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

10.0 out of 10, Exceptional, (126)
"We had an excellent stay! The property and all the added touches made our stay relaxing and low stress. The host was engaging and helpful if we had questions. We would stay here again!"
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Condo with Pool and Beach Access
Terrace/patio

Condo with Pool and Beach Access

10.0 out of 10, Exceptional, (22)
"We liked everything about the property. This is a quite end unit and was nicely finished. Would definitely highly recommend staying here."
Condo with Pool and Beach Access
Castaway Key, Double balcony ocean views in prime building 4
Outdoor pool, a heated pool

Castaway Key, Double balcony ocean views in prime building 4

10.0 out of 10, Exceptional, (126)
"Beautiful view. Nice staying. I would recommend this place 100%"
Castaway Key, Double balcony ocean views in prime building 4
Luxury Condo at Ocean Front Kawama Tower Complex
Property grounds

Luxury Condo at Ocean Front Kawama Tower Complex

9.4 out of 10, Exceptional, (55)
"Very clean and spacious condo. Pool area very quiet and relaxing - no crowds. Enjoyed the pickle ball courts. Quick drive to restaurants."
Luxury Condo at Ocean Front Kawama Tower Complex
Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball
Property grounds

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball

10.0 out of 10, Exceptional, (35)
"Great place to take your family and enjoy doing nothing but relaxing by the pool or on the beach. "
Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball
Relax & Recharge at our Quiescent 2 BR Condo with Stunning Ocean Views
On the beach, sun-loungers, beach towels

Relax & Recharge at our Quiescent 2 BR Condo with Stunning Ocean Views

9.8 out of 10, Exceptional, (88)
"Everything was great"
Relax & Recharge at our Quiescent 2 BR Condo with Stunning Ocean Views
Relaxed Boho Vibes & Views [ Ocean Pointe 2315]
Outdoor pool, a heated pool

Relaxed Boho Vibes & Views [ Ocean Pointe 2315]

9.8 out of 10, Exceptional, (172)
"Loved the pool and the condo was comfortable "
Relaxed Boho Vibes & Views [ Ocean Pointe 2315]
Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!
Marina

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

9.8 out of 10, Exceptional, (50)
"The property was clean and spacious. "
Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
On the beach, beach towels

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

9.6 out of 10, Exceptional, (207)
"Very nice place to stay."
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!
Property grounds

Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!

9.6 out of 10, Exceptional, (287)
"Visited with my Mother, sister and cousin. Felt very safe with the gated security. The grounds were beautiful and very well maintained. Location was great! The beach, marina, pool were all very close by. And the condo was fabulous and very well stocked."
Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!
Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (33)
"The place is as advertised. It's much more of a laid back quiet experience which we enjoyed.The unit itself is beautiful, spacious, and easily accommodateed our family of 5."
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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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled. "
James 2-night trip
Posted 14 hours ago
Chesapeake Beach Resort