A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Upper Matecumbe Key condo rentals

A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

1. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (37 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
$275 nightly
The price is $305
Sep 2 - Sep 3
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

2. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
$315 nightly
The price is $349
Aug 23 - Aug 24
Total with taxes and fees
Amazing Ocean view condo
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

3. Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA

Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay! The space had everything we needed and was very comfortable. It is spacious, has an excellent bed and updated finishes. The pool is a great spot to hang out with plenty of chairs. The management team was very helpful and responsive to all of our needs (even on the 4th holiday!). Would definitely stay again."
United States
Chris
$374 nightly
The price is $404
Aug 31 - Sep 1
Total with taxes and fees
Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

4. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
$372 nightly
The price is $413
Aug 23 - Aug 24
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

5. Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (135 reviews)
"Very clean and comfortable, wonderful amenities, great view of the ocean, fantastic location and the hosts were so accessible and helpful. We thoroughly enjoyed our stay!"
United States
Deborah D.
$410 nightly
The price is $444
Aug 23 - Aug 24
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307
A beach resort with a clear view of the ocean, a thatched-roof hut, and a building with a blue roof.

6. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
$386 nightly
The price is $418
Sep 8 - Sep 9
Total with taxes and fees
Flamingo Flats Ocean Pointe 5306 2BR/2BA
A bay window with two chairs, a table, and a view of a beach with palm trees and a flag.

7. Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (17 reviews)
"Loved this condo. Had all the amenities we needed and was super clean and tidy. Will definitely be staying here again. "
United States
Rodney B.
$381 nightly
The price is $415
Aug 23 - Aug 24
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315
A waterfront property with a dock, a boat, and a building with a blue roof.

8. Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Tavernier
9.6 out of 10, Exceptional, (33 reviews)
"The apartment was perfect, great location over looking the ocean, and nice and clean. They had everything we needed for our stay, The pool and the hot tub at the resort where clean and welcoming."
United States
Kimberly P.
$457 nightly
The price is $507
Aug 24 - Aug 25
Total with taxes and fees
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
A beachside area with wooden benches, a thatched roof structure, and directional signs for various locations.

9. Ocean View Retreat w/Private Pool, 2 Br Condo, Lagoon, Kayaks, Marina, Sunrises!

Ocean View Retreat w/Private Pool, 2 Br Condo, Lagoon, Kayaks, Marina, Sunrises!
Key Largo
10.0 out of 10, Exceptional, (1 review)
"The condo was clean, comfortable, and exactly as described. The host was friendly, responsive, and made the entire experience easy from check-in to check-out. We truly appreciated the hospitality and would definitely stay here again. Highly recommend!"
United States
Gladys M.
$488 nightly
The price is $541
Aug 24 - Aug 25
Total with taxes and fees
Ocean View Retreat w/Private Pool, 2 Br Condo, Lagoon, Kayaks, Marina, Sunrises!
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

10. Coral Penthouse Key Largo Ocean Pointe 4216

Coral Penthouse Key Largo Ocean Pointe 4216
Tavernier
10.0 out of 10, Exceptional, (20 reviews)
"The ocean view was perfect. The property was nicely situated for all the activities and restaurants in the upper keys. Would definitely stay here again"
United States
David C.
$408 nightly
The price is $442
Aug 29 - Aug 30
Total with taxes and fees
Coral Penthouse Key Largo Ocean Pointe 4216
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building with a blue roof.

11. Key Largo 1BR - Ocean View, Near Founders Park

Key Largo 1BR - Ocean View, Near Founders Park
Tavernier
8.0 out of 10, Very Good, (1 review)
"Overall, the room was very clean and well kept, and the check in process was quite easy with only a small hiccup (didn't know we had to go to a different location to pick up the key for the room, but it wasn't too far away). The only downside is that the first bullet point on the listing says "private beach," which I guess in the sense is not wrong, but it is very small area that is not well kept, and has a lot of rotting seaweed, which makes the "beach" quite undesirable. I guess for this time...
United States
Manasa R.
$317 nightly
The price is $352
Aug 24 - Aug 25
Total with taxes and fees
Key Largo 1BR - Ocean View, Near Founders Park
A beach with turquoise chairs, a wooden walkway, and a thatched-roof structure.

12. Ocean Pointe - Pool, Hot Tub, View, Beach, Parking

Ocean Pointe - Pool, Hot Tub, View, Beach, Parking
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Nelson was very responsive and a wonderful host. The unit was excellent! The best we have ever stayed in. We will most certainly be back "
United States
barbara m.
$311 nightly
The price is $345
Sep 14 - Sep 15
Total with taxes and fees
Ocean Pointe - Pool, Hot Tub, View, Beach, Parking
A beach resort with a clear view of the ocean, a thatched-roof hut, and a building with a blue roof.

13. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
$415 nightly
The price is $450
Aug 24 - Aug 25
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
A beach resort with a clear view of the ocean, a thatched-roof hut, and a building with a blue roof.

14. Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
$379 nightly
The price is $412
Aug 26 - Aug 27
Total with taxes and fees
Reel Key Largo Escape Ocean Pointe 5209
A waterfront property with a dock leading to a building with a blue roof, surrounded by palm trees and a clear sky.

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

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (29 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
$410 nightly
The price is $445
Aug 26 - Aug 27
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
A pool area with a palm tree, a showerhead, and blue lounge chairs.

16. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great place"
United States
mike c.
$297 nightly
The price is $330
Sep 8 - Sep 9
Total with taxes and fees
Ocean Pointe Ocean View w/heated pool beach marina

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

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
9.8 out of 10, Exceptional, (9 reviews)
"An awesome place to stay, fish and relax!"
United States
robert d.
$389 nightly
The price is $423
Aug 22 - Aug 23
Total with taxes and fees
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
A beach resort with a clear view of the ocean, a thatched-roof hut, and a building with a blue roof.

18. Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (27 reviews)
"Great place to stay and if you are fishing this is the building closest to the fish cleaning station."
United States
Justin C.
$412 nightly
The price is $447
Aug 25 - Aug 26
Total with taxes and fees
Ocean View Overlooking Marina Ocean Pointe 5305
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

19. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
$366 nightly
The price is $406
Aug 23 - Aug 24
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A modern showerhead with multiple water streams, a tiled wall, and a pool area with blue chairs and a palm tree.

20. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
$358 nightly
The price is $397
Aug 27 - Aug 28
Total with taxes and fees
Ocean view condo with balcony/marina 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.
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Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Definitely a top 5 hotel. I wish it had a close dedicated dog area. But i know space is limited. We were told to take the dog to the golf course. So if you are a golfer, watch your step."
Elizabeth 5-night trip
Posted 1 hour ago
Cheeca Lodge & Spa

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Rentals information

Number of reviews
709
Accommodation
357 Condo Rentals
Lowest Price
$305
Highest Price
$541

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