Search Upper Matecumbe Key Condo Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Upper Matecumbe Key condo rentals

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (18)
"Everything was just as described in the condo listing. We enjoyed the pool and hot tub. Wonderful location to explore the Keys. "
United States
Michele G.
The price is €370
includes taxes & fees
26 Dec - 27 Dec
Florida Keys Getaway - Slps 4 - Ocean View

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (42)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
The price is €329
includes taxes & fees
4 Jan - 5 Jan 2026
Amazing Ocean view condo

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.6 out of 10, Exceptional, (15)
"This condo was everything we needed. Lots of space, bug comfy beds, hreat shower and the pool at the complex was great in the late afternoon after a day exploring the upper keys. There were works going on at the conplex when we were there which took the edge off things as 9am drilling on Monday morning wasnt welcome but I only knocked 1 star off - otherwise wouldnt hesitate to recommend!"
United Kingdom
Philippa
The price is €391
includes taxes & fees
7 Jan - 8 Jan 2026
Blue Haven Key Largo | Ocean Pointe 1315

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (122)
"We enjoyed our stay!"
United States
Halley R.
The price is €363
includes taxes & fees
19 Jan - 20 Jan 2026
Modern and Coastal Ocean Pointe 2307

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is €416
includes taxes & fees
5 Jan - 6 Jan 2026
Serenity In The Sun Condo Fabulous Ocean View

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
The price is €399
includes taxes & fees
20 Jan - 21 Jan 2026
Lazy Daze Double King Suite Ocean Pointe 2310

Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (7)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is €423
includes taxes & fees
14 Jan - 15 Jan 2026
Flamingo Flats Ocean Pointe 5306 2BR/2BA

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (42)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
The price is €372
includes taxes & fees
4 Jan - 5 Jan 2026
Ocean view condo with balcony/marina view

Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (1)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is €418
includes taxes & fees
18 Jan - 19 Jan 2026
Aqua Vista Ocean Pointe 3307

1BR w/ Partial Ocean View, Pool & Beach

1BR w/ Partial Ocean View, Pool & Beach
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (3)
"Loved the property and its central location. Fairly quiet and secluded. Incredible views and the complex has everything you need for a nice relaxing vacation. With the prices they offer, I can’t recommend it enough!"
United States
Andrew W.
1BR w/ Partial Ocean View, Pool & Beach

Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (13)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
The price is €423
includes taxes & fees
12 Jan - 13 Jan 2026
Captains Quarters Ocean Pointe 4405

Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities

Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities
Blue Waters
9.4 out of 10, Exceptional, (24)
"Unit was everything we hoped for, building was nice, quiet, and had good amenities, and the grounds and pool were great. Would absolutely stay here again on future trips."
United States
Jacob W.
The price is €674
includes taxes & fees
8 Jan - 9 Jan 2026
Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities

Sea View Farm Style Ocean front Condo Views

Sea View Farm Style Ocean front Condo Views
Tavernier
10.0 out of 10, Exceptional, (154)
"The property was excellent."
United States
June M.
The price is €389
includes taxes & fees
5 Jan - 6 Jan 2026
Sea View Farm Style Ocean front Condo Views

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

Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys
Tavernier
9.8 out of 10, Exceptional, (161)
"place was great. wish the price of using the dock would be known before I booked it,"
United States
Duffy P.
The price is €559
includes taxes & fees
13 Jan - 14 Jan 2026
Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
2.0 star property
Tavernier
10.0 out of 10, Exceptional, (3)
"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."
United States
Kevin W.
The price is €479
includes taxes & fees
21 Jan - 22 Jan 2026
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (24)
"This was a wonderful place to stay in the Florida Keys. The location was beautiful. We watched sunrise each morning from the balcony. The unit faced the ocean. We would certainly stay here again."
United States
Donald
The price is €444
includes taxes & fees
21 Jan - 22 Jan 2026
Ocean View Overlooking Marina Ocean Pointe 5305

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (12)
"Perfect Stay."
United States
suhaela s.
The price is €500
includes taxes & fees
4 Jan - 5 Jan 2026
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR

Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR
Tavernier
9.4 out of 10, Exceptional, (48)
"clean great location "
United States
Tracey A.
The price is €719
includes taxes & fees
31 Dec - 1 Jan 2026
Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR

{PRIVATELY OWNED} This 2 bedroom has everything you need. with a Fantastic view.

{PRIVATELY OWNED} This 2 bedroom has everything you need. with a Fantastic view.
Tavernier
9.8 out of 10, Exceptional, (108)
"Clean, everything we needed.The property, especially the pool and restaurant were excellent. We had a great time."
United States
Lenny F.
The price is €401
includes taxes & fees
11 Jan - 12 Jan 2026
{PRIVATELY OWNED} This 2 bedroom has everything you need. with a Fantastic view.

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
2.0 star property
Blue Waters
10.0 out of 10, Exceptional, (2)
"Beautifully high-end decorated & furnished like brand new! Very clean and appointed with everything one could want for a perfect stay. First floor convenience (building elevated on piers) but no water view Would definitely return! "
United States
Peter A. Z.
The price is €427
includes taxes & fees
19 Jan - 20 Jan 2026
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Rentals information

Number of reviews
870
Accommodation
390 Condo Rentals
Lowest Price
€329
Highest Price
€719

Explore a world of travel with Expedia