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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Condo Rentals in Upper Matecumbe Key

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. "
Key Largo Ocean Shore Villa 1 with pool & boat slip
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 AU$695
includes taxes & fees
24 Aug - 25 Aug
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 AU$651
includes taxes & fees
24 Aug - 25 Aug
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
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 AU$616
includes taxes & fees
24 Aug - 25 Aug
Serenity In The Sun Condo Fabulous Ocean View
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 AU$690
includes taxes & fees
24 Aug - 25 Aug
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 AU$675
includes taxes & fees
24 Aug - 25 Aug
Aqua Vista Ocean Pointe 3307
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 AU$675
includes taxes & fees
24 Aug - 25 Aug
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Lazy Daze Double King Suite Ocean Pointe 2310
Pool

Lazy Daze Double King Suite Ocean Pointe 2310

9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
The price is AU$675
includes taxes & fees
24 Aug - 25 Aug
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 AU$655
includes taxes & fees
24 Aug - 25 Aug
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 AU$675
includes taxes & fees
24 Aug - 25 Aug
Blue Haven Key Largo | Ocean Pointe 1315
2BR Condo w/ Ocean View, Pool & Tropical Setting
Marina

2BR Condo w/ Ocean View, Pool & Tropical Setting

2.0 star property
9.4 out of 10, Exceptional, (3)
" centrally located for keys travel"
The price is AU$469
includes taxes & fees
3 Sept - 4 Sept
2BR Condo w/ Ocean View, Pool & Tropical Setting
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 AU$726
includes taxes & fees
25 Aug - 26 Aug
Ocean View Treehouse Double King Suite 3403
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!"
Captains Quarters Ocean Pointe 4405
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 AU$680
includes taxes & fees
1 Sept - 2 Sept
Ocean View Overlooking Marina Ocean Pointe 5305
Amazing Ocean view condo
Pool

Amazing Ocean view condo

9.6 out of 10, Exceptional, (40)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
The price is AU$613
includes taxes & fees
25 Aug - 26 Aug
Amazing Ocean view condo
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 AU$720
includes taxes & fees
23 Aug - 24 Aug
Ocean view condo with balcony/marina view
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 AU$645
includes taxes & fees
26 Aug - 27 Aug
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
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 AU$703
includes taxes & fees
1 Sept - 2 Sept
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Toes in the Sand - 2 Bedroom Condo Sleeps 4
Terrace/patio

Toes in the Sand - 2 Bedroom Condo Sleeps 4

10.0 out of 10, Exceptional, (26)
"A great first stop on our trip to the Keys! Instructions were great and the condo was very nice."
Toes in the Sand - 2 Bedroom Condo Sleeps 4
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 AU$610
includes taxes & fees
24 Aug - 25 Aug
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.
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Top Upper Matecumbe Key Hotel Reviews

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Wonderful Southern Florida type cottages. Super quiet and well kept grounds. The rooms show some wear but otherwise a great stay. "
Ramona 3-night trip
Posted 19 hours ago
La Siesta Resort & Villas