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

Search Upper Matecumbe Key Condo Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
The price is AU$457
includes taxes & fees
3 Nov - 4 Nov
Florida Keys Getaway - Slps 4 - Ocean View
A living room with a blue sofa, a glass coffee table, and a lamp. There is a kitchen in the background with a refrigerator, microwave, and stove.

2. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 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.
The price is AU$487
includes taxes & fees
29 Oct - 30 Oct
Amazing Ocean view condo
Property grounds

3. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is AU$582
includes taxes & fees
5 Nov - 6 Nov
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Perfect spot to stay in the keys! Great for fishing. The condo had everything you need to make your stay amazing. We will be back! Check in and out was a breeze, guards at gate were super friendly!"
United States
Pam K.
The price is AU$504
includes taxes & fees
29 Oct - 30 Oct
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A balcony with a table and chairs, a sofa, and a lamp.

5. Ocean View Gem | 2 Balconies | Ocean Pointe 3406

Ocean View Gem | 2 Balconies | Ocean Pointe 3406
Tavernier
9.8 out of 10, Exceptional, (11 reviews)
"Clean and perfect location"
United States
Joanne P.
Ocean View Gem | 2 Balconies | Ocean Pointe 3406
A resort with multiple buildings, a swimming pool, tennis courts, and a view of the ocean.

6. Paradise Palms | 2 Balconies | Ocean Pointe 1206

Paradise Palms | 2 Balconies | Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is AU$600
includes taxes & fees
27 Oct - 28 Oct
Paradise Palms | 2 Balconies | Ocean Pointe 1206
A spacious living area with a sofa, chairs, a coffee table, and a balcony with a view.

7. 1BR Condo w/ Ocean View, Near Coral Reef Park

1BR Condo w/ Ocean View, Near Coral Reef Park
Tavernier
The price is AU$536
includes taxes & fees
1 Nov - 2 Nov
1BR Condo w/ Ocean View, Near Coral Reef Park
A beachside lounge with lounge chairs and a wooden deck overlooking the ocean.

8. 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
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
The price is AU$619
includes taxes & fees
3 Nov - 4 Nov
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

9. Sea Glass & Sunshine | 2BR | Ocean Pointe 2207

Sea Glass & Sunshine | 2BR | Ocean Pointe 2207
Tavernier
10.0 out of 10, Exceptional, (1 review)
"Nice property, enjoyed the pool and the on-site bar / restaurant"
United States
Scott S.
The price is AU$580
includes taxes & fees
1 Nov - 2 Nov
Sea Glass & Sunshine | 2BR | Ocean Pointe 2207
A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is AU$511
includes taxes & fees
1 Nov - 2 Nov
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A spacious living room with a large window, a wooden coffee table with a floral rug, a sofa, and a balcony with a view.

11. 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 location and host is great with communication!"
United States
Mary Katherine B.
The price is AU$487
includes taxes & fees
1 Nov - 2 Nov
Ocean Pointe Ocean View w/heated pool beach marina
Property grounds

12. Across from Pool | Sleeps 6 | Ocean Pointe 3212

Across from Pool | Sleeps 6 | Ocean Pointe 3212
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Wonderful location, great amenities on site- pool, pool bar, hammocks, grills. Very comfortable condo! Thank you!! We plan to come again!"
United States
Kelly S.
The price is AU$647
includes taxes & fees
1 Nov - 2 Nov
Across from Pool | Sleeps 6 | Ocean Pointe 3212
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

13. Starfish Seas | Ocean View | Ocean Pointe 1302

Starfish Seas | Ocean View | Ocean Pointe 1302
Tavernier
9.8 out of 10, Exceptional, (30 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.
The price is AU$630
includes taxes & fees
30 Oct - 31 Oct
Starfish Seas | Ocean View | Ocean Pointe 1302
A waterfront property with a dock leading to a building with a blue roof.

14. Reel Key Largo | Next to Pool | Ocean Pointe 5209

Reel Key Largo | Next to Pool | 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.
The price is AU$592
includes taxes & fees
1 Nov - 2 Nov
Reel Key Largo | Next to Pool | Ocean Pointe 5209
A spacious living room with a large window, a ceiling fan, a sofa, two armchairs, a coffee table, and a side table with lamps.

15. 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.
The price is AU$630
includes taxes & fees
31 Oct - 1 Nov
Lazy Daze | Double King Suite | Ocean Pointe 2310
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

16. Blue Haven | Nature View 2BR | Ocean Pointe 1315

Blue Haven | Nature View 2BR | 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.
The price is AU$600
includes taxes & fees
27 Oct - 28 Oct
Blue Haven | Nature View 2BR | Ocean Pointe 1315
A wooden pier leading to a thatched-roof structure with outdoor seating.

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

Ocean Pointe - Pool, Hot Tub, View, Beach, Parking
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and comfortable!"
United States
Justin D.
The price is AU$537
includes taxes & fees
27 Oct - 28 Oct
Ocean Pointe - Pool, Hot Tub, View, Beach, Parking
A wooden deck with chairs and a table, overlooking the ocean.

18. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
The price is AU$562
includes taxes & fees
1 Nov - 2 Nov
Ocean view condo with balcony/marina view
A room with two armchairs, a small table, and a sofa, all facing large windows with a view of the ocean.

19. Ocean View Treehouse | 2 Kings | Ocean Pointe 3403

Ocean View Treehouse | 2 Kings | Ocean Pointe 3403
Tavernier
10.0 out of 10, Exceptional, (3 reviews)
"Great location and the condo was well done. Everything was great. We specifically choose this property because it had 2 king size beds. Everything was exactly as advertised."
United States
Mike P.
The price is AU$669
includes taxes & fees
1 Nov - 2 Nov
Ocean View Treehouse | 2 Kings | Ocean Pointe 3403
A wooden deck with a thatched roof, overlooking the sea.

20. Toes in the Sand - 2 Bedroom Condo Sleeps 4

Toes in the Sand - 2 Bedroom Condo Sleeps 4
Tavernier
10.0 out of 10, Exceptional, (51 reviews)
"Super clean great location"
United States
Gary C.
The price is AU$578
includes taxes & fees
31 Oct - 1 Nov
Toes in the Sand - 2 Bedroom Condo Sleeps 4
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Great property however the rooms could use an update."
Michelle 2-night trip
Posted 2 hours ago
Amara Cay Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Rentals information

Number of reviews
516
Accommodation
359 Condo Rentals
Lowest Price
AU$457
Highest Price
AU$669

Explore a world of travel with Expedia