Search Condos Rentals in Upper Matecumbe Key from CA $206

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Upper Matecumbe Key Condo Rentals

Key Largo Ocean Shore Villa 1 with pool & boat slip
Smart TV

Key Largo Ocean Shore Villa 1 with pool & boat slip

9.6 out of 10, Exceptional, (130)
"The apartment was excellent and just as described. Very clean, well equipped, with comfortable beds. We had a great time. "
The price is CA $350
CA $738 total
includes taxes & fees
Aug 24 - Aug 25
Key Largo Ocean Shore Villa 1 with pool & boat slip
Serenity In The Sun Condo Fabulous Ocean View
A heated pool

Serenity In The Sun Condo Fabulous Ocean View

10.0 out of 10, Exceptional, (104)
"Good clean condo, great pool and little private beach "
The price is CA $206
CA $541 total
includes taxes & fees
Aug 19 - Aug 20
Serenity In The Sun Condo Fabulous Ocean View
Modern and Coastal Ocean Pointe 2307
Pool

Modern and Coastal Ocean Pointe 2307

10.0 out of 10, Exceptional, (121)
"Everything was extremely efficient both with check in and check out processes. The condo was clean and the property in general was in tip top shape. The pool was great and my kids caught a lot of fish in the marina. I would highly recommend. We did not have any issues, but if we would have I feel that the "
The price is CA $231
CA $610 total
includes taxes & fees
Aug 19 - Aug 20
Modern and Coastal Ocean Pointe 2307
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Pool

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

9.8 out of 10, Exceptional, (25)
"Accommodation and location are excellent! Listing is accurate and the resort amenities are very enjoyable after a day out exploring the Keys (or just having at least one whole day at the resort, as we did). "
The price is CA $202
CA $572 total
includes taxes & fees
Aug 19 - Aug 20
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Coastal comfort in Ocean Pointe Suites.
On the beach, sun loungers, beach towels

Coastal comfort in Ocean Pointe Suites.

10.0 out of 10, Exceptional, (33)
"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "
The price is CA $272
CA $817 total
includes taxes & fees
Sep 2 - Sep 3
Coastal comfort in Ocean Pointe Suites.
2BR w/ Ocean Views, Pool, Beach, Near Pennekamp Park
Beach

2BR w/ Ocean Views, Pool, Beach, Near Pennekamp Park

2.0 star property
8.0 out of 10, Very good, (2)
"The apt was ok for the priced paid. Location was great and so were amenities. There is a nice on-site pool, kayas and restaurant. Check in was easy but had an issue with management charging me more than what i paid on VRBO. Be aware of what you sign and your total matching! Would stay in this community again but will rent via Airb&b next time , from an owner. "
The price is CA $212
CA $383 total
includes taxes & fees
Sep 3 - Sep 4
2BR w/ Ocean Views, Pool, Beach, Near Pennekamp Park
Gorgeous oceanfront retreat with marina, pool, & ocean views
A heated pool

Gorgeous oceanfront retreat with marina, pool, & ocean views

9.0 out of 10, Wonderful, (68)
"I love that this resort had its own private Beach area, pier, restaurant, and pool area!"
The price is CA $137
CA $606 total
includes taxes & fees
Aug 24 - Aug 25
Gorgeous oceanfront retreat with marina, pool, & ocean views
Aqua Vista Ocean Pointe 3307
Pool

Aqua Vista Ocean Pointe 3307

2.5 star property
10.0 out of 10, Exceptional, (1)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
The price is CA $217
CA $593 total
includes taxes & fees
Aug 19 - Aug 20
Aqua Vista Ocean Pointe 3307
Lazy Daze Double King Suite Ocean Pointe 2310
Pool

Lazy Daze Double King Suite Ocean Pointe 2310

9.6 out of 10, Exceptional, (25)
"Everything was exceptionally nice. Would definitely book again."
The price is CA $217
CA $593 total
includes taxes & fees
Aug 19 - Aug 20
Lazy Daze Double King Suite Ocean Pointe 2310
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Pool

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

9.6 out of 10, Exceptional, (5)
"Thanks for your great hospitality."
The price is CA $203
CA $575 total
includes taxes & fees
Aug 19 - Aug 20
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Blue Haven Key Largo | Ocean Pointe 1315
Pool

Blue Haven Key Largo | Ocean Pointe 1315

9.6 out of 10, Exceptional, (14)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
The price is CA $217
CA $593 total
includes taxes & fees
Aug 19 - Aug 20
Blue Haven Key Largo | Ocean Pointe 1315
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Pool

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

2.0 star property
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."
The price is CA $217
CA $593 total
includes taxes & fees
Aug 25 - Aug 26
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Captains Quarters Ocean Pointe 4405
Pool

Captains Quarters Ocean Pointe 4405

10.0 out of 10, Exceptional, (13)
"Great location, accommodations and communication. Great to have a pool on the property for the kids. Would definitely stay again!"
The price is CA $246
CA $627 total
includes taxes & fees
Aug 25 - Aug 26
Captains Quarters Ocean Pointe 4405
Ocean View Treehouse Double King Suite 3403
Pool

Ocean View Treehouse Double King Suite 3403

10.0 out of 10, Exceptional, (1)
"Clean, comfortable and cozy! Just what we hoped for!"
The price is CA $246
CA $630 total
includes taxes & fees
Aug 20 - Aug 21
Ocean View Treehouse Double King Suite 3403
Ocean View Overlooking Marina Ocean Pointe 5305
Pool

Ocean View Overlooking Marina Ocean Pointe 5305

10.0 out of 10, Exceptional, (23)
"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."
The price is CA $217
CA $593 total
includes taxes & fees
Aug 19 - Aug 20
Ocean View Overlooking Marina Ocean Pointe 5305
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Sun loungers, beach towels

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

9.8 out of 10, Exceptional, (9)
"Sandra was very communicative and made the check in/check out process very easy. The condo was perfect for our family of 4. We only stayed for 2 nights on a road trip from Key West to Fort Lauderdale and we would have loved to stay longer. Hopefully we can come back soon! "
The price is CA $198
CA $560 total
includes taxes & fees
Aug 19 - Aug 20
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Ocean Pointe Ocean View w/heated pool beach marina
Terrace/patio

Ocean Pointe Ocean View w/heated pool beach marina

9.0 out of 10, Wonderful, (9)
"The property is naturally beautiful, safe, and secluded! The staff, especially Alex and Alex, are amazing! Thank you, Alex, for making our stay--for the 4th time--a great one! "
The price is CA $277
CA $449 total
includes taxes & fees
Sep 2 - Sep 3
Ocean Pointe Ocean View w/heated pool beach marina
Ocean view condo with balcony/marina view
Terrace/patio

Ocean view condo with balcony/marina view

8.8 out of 10, Excellent, (41)
"As advertised "
The price is CA $311
CA $632 total
includes taxes & fees
Aug 19 - Aug 20
Ocean view condo with balcony/marina view
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Beach

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"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! "
The price is CA $232
CA $618 total
includes taxes & fees
Sep 1 - Sep 2
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Sea View Farm Style Ocean front Condo Views
Pool

Sea View Farm Style Ocean front Condo Views

10.0 out of 10, Exceptional, (151)
"The place was ready, clean, well organized and the owners were easy to reach on the phone"
The price is CA $206
CA $536 total
includes taxes & fees
Aug 19 - Aug 20
Sea View Farm Style Ocean front Condo Views
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
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

10/10 Excellent
"Amazing stay! The staff was super friendly, rooms were clean and comfortable, and the pool/tiki bar gave off the perfect Key Largo vibe. Great location close to everything. Definitely coming back!"
Meiling 1-night trip
Posted 22 hours ago
Holiday Inn Key Largo by IHG