Photo by Cameron Abbott

Search and Rent Upper Matecumbe Key Condos

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Upper Matecumbe Key condo rentals

Pool
Amazing Ocean view condo

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.
$310 nightly
The price is $344
Dec 16 - Dec 17
Total with taxes and fees
Amazing Ocean view condo
Exterior
Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.6 out of 10, Exceptional, (18)
"Room and location were great! Community pool was very nice and we used it a lot. Quick walk down to the marina. We would stay here again."
United States
Kyle W.
$295 nightly
The price is $327
Dec 19 - Dec 20
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
On the beach
Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View

Serenity In The Sun Condo Fabulous Ocean View
Tavernier
10.0 out of 10, Exceptional, (107)
"Good clean condo, great pool and little private beach "
United Kingdom
Nicola W.
$434 nightly
The price is $482
Jan 5 - Jan 6, 2026
Total with taxes and fees
Serenity In The Sun Condo Fabulous Ocean View
Beach
Aqua Vista Ocean Pointe 3307

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
$416 nightly
The price is $452
Dec 21 - Dec 22
Total with taxes and fees
Aqua Vista Ocean Pointe 3307
Beach nearby
Flamingo Flats Ocean Pointe 5306 2BR/2BA

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.
$384 nightly
The price is $417
Dec 17 - Dec 18
Total with taxes and fees
Flamingo Flats Ocean Pointe 5306 2BR/2BA
Beach nearby
Blue Haven Key Largo | Ocean Pointe 1315

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
$385 nightly
The price is $419
Dec 16 - Dec 17
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315
Beach
1BR w/ Partial Ocean View, Pool & Beach

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.
$298 nightly
The price is $331
Dec 16 - Dec 17
Total with taxes and fees
1BR w/ Partial Ocean View, Pool & Beach
Beach nearby
Lazy Daze Double King Suite Ocean Pointe 2310

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
$395 nightly
The price is $429
Dec 16 - Dec 17
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
Beach nearby
Modern and Coastal Ocean Pointe 2307

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.
$388 nightly
The price is $421
Dec 16 - Dec 17
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307
A heated pool
OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.4 out of 10, Very Good, (11)
"Great place"
United States
mike c.
OP-2 Ocean View w/heated pool beach marina
Beach
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

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.
$395 nightly
The price is $429
Dec 16 - Dec 17
Total with taxes and fees
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
A heated pool
Ocean view condo with balcony/marina view

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
$387 nightly
The price is $429
Dec 16 - Dec 17
Total with taxes and fees
Ocean view condo with balcony/marina view
Beach nearby
Captains Quarters Ocean Pointe 4405

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.
$420 nightly
The price is $457
Dec 19 - Dec 20
Total with taxes and fees
Captains Quarters Ocean Pointe 4405
Beach nearby
Ocean View Overlooking Marina Ocean Pointe 5305

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
$385 nightly
The price is $419
Dec 16 - Dec 17
Total with taxes and fees
Ocean View Overlooking Marina Ocean Pointe 5305
Beach
Sea View Farm Style Ocean front Condo Views

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.
$395 nightly
The price is $439
Dec 16 - Dec 17
Total with taxes and fees
Sea View Farm Style Ocean front Condo Views
Sun loungers, beach towels
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

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.
$473 nightly
The price is $525
Dec 20 - Dec 21
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Beach
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

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.
$398 nightly
The price is $432
Dec 16 - Dec 17
Total with taxes and fees
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Marina
Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR

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.
$833 nightly
The price is $926
Dec 31 - Jan 1, 2026
Total with taxes and fees
Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR
TV
Ocean View Treehouse Double King Suite 3403

Ocean View Treehouse Double King Suite 3403

Ocean View Treehouse Double King Suite 3403
Tavernier
10.0 out of 10, Exceptional, (2)
"Clean, comfortable and cozy! Just what we hoped for!"
Canada
Richard G.
$420 nightly
The price is $456
Dec 16 - Dec 17
Total with taxes and fees
Ocean View Treehouse Double King Suite 3403
Marina
{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.

{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.
$412 nightly
The price is $458
Jan 11 - Jan 12, 2026
Total with taxes and fees
{PRIVATELY OWNED} This 2 bedroom has everything you need. with a Fantastic view.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Casa Morada

Casa Morada

10/10 Excellent
"Room was clean. Facility beautiful. Staff wonderful!"
Michael 3-night trip
Posted 4 days ago
Casa Morada

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Rentals information

Number of reviews
723
Accommodation
390 Condo Rentals
Lowest Price
$327
Highest Price
$926

Explore a world of travel with Expedia