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

Search Condo Rentals in Upper Matecumbe Key

  • 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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (41 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 HK$841
HK$2,626 total
includes taxes & fees
3 Nov - 4 Nov
Florida Keys Getaway - Slps 4 - Ocean View
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (172 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 HK$981
HK$2,791 total
includes taxes & fees
14 Oct - 15 Oct
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

4. 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 HK$1,059
HK$2,703 total
includes taxes & fees
12 Oct - 13 Oct
Amazing Ocean view condo
A resort with multiple buildings, a swimming pool, tennis courts, and a view of the ocean.

5. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
The price is HK$1,221
HK$3,247 total
includes taxes & fees
9 Nov - 10 Nov
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
A kitchen with granite countertops, a dining area with a table and chairs, a balcony with a view, and a bedroom visible through an open door.

6. 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.
The price is HK$1,174
HK$3,168 total
includes taxes & fees
10 Nov - 11 Nov
Reel Key Largo Escape Ocean Pointe 5209
Beach

7. Aqua Vista Ocean Pointe 3307

Aqua Vista 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 HK$1,135
HK$3,239 total
includes taxes & fees
10 Nov - 11 Nov
Aqua Vista Ocean Pointe 3307
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

8. 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
The price is HK$1,057
HK$3,031 total
includes taxes & fees
1 Nov - 2 Nov
Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
A beachside resort with a thatched umbrella, palm trees, and a dock.

9. 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 HK$1,339
HK$3,511 total
includes taxes & fees
15 Oct - 16 Oct
Lazy Daze Double King Suite Ocean Pointe 2310
A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a gazebo.

10. Family-Friendly 1BR w/ Partial Ocean View & Pool

Family-Friendly 1BR w/ Partial Ocean View & Pool
Tavernier
Family-Friendly 1BR w/ Partial Ocean View & Pool
A pool area with a palm tree, a showerhead, and blue lounge chairs.

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 HK$1,483
HK$2,674 total
includes taxes & fees
10 Nov - 11 Nov
Ocean Pointe Ocean View w/heated pool beach marina
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

12. 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.
The price is HK$1,214
HK$3,238 total
includes taxes & fees
10 Nov - 11 Nov
Blue Haven Key Largo | Ocean Pointe 1315
A modern showerhead with multiple water streams, a tiled wall, and a pool area with blue chairs and a palm tree.

13. 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 HK$1,398
HK$3,131 total
includes taxes & fees
11 Oct - 12 Oct
Ocean view condo with balcony/marina view
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

14. 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, (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 HK$1,339
HK$3,511 total
includes taxes & fees
12 Oct - 13 Oct
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
A hotel room with a bed, a wicker chest of drawers, a white door, and a framed picture on the wall.

15. Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201

Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
Tavernier
10.0 out of 10, Exceptional, (1 review)
"This was a great unit for our purpose. Felt newly remodeled. Beds were comfy. Nice extras provided, like a cooler, pool noodles, pickleball, tennis rackets and some fishing gear. Check in & out was one of the easiest, so far. The pool was a HUGE hit. Location was good. Close to the park and good food. Husband only wished we were a bit closer to fishing, but we just didn’t know. Only critiques; wish the couch was a bit bigger. It isn’t bad, just a note. And the patio is small and the furniture...
United States
Cara B.
The price is HK$1,386
HK$3,592 total
includes taxes & fees
13 Oct - 14 Oct
Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
Beach

16. 3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
The price is HK$1,410
HK$3,602 total
includes taxes & fees
12 Oct - 13 Oct
3212 Across from Pool * King & Queen/Twin Bunk Bed
A beach with clear shallow water, a sandy shore, and trees.

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

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"Clean and perfect location"
United States
Joanne P.
The price is HK$1,269
HK$3,420 total
includes taxes & fees
11 Oct - 12 Oct
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
A beach with thatched umbrellas, lounge chairs, and palm trees.

18. Coastal Retreat, Pool, Marina, Ocean View, FL Keys

Coastal Retreat, Pool, Marina, Ocean View, FL Keys
Tavernier
10.0 out of 10, Exceptional, (1 review)
" Perfect Florida Keys Getaway!We had an amazing stay at this Ocean Pointe condo in Tavernier! The unit was spotless, beautifully decorated, and equipped with everything we needed for a comfortable vacation. The beds were comfortable, the kitchen was well stocked, and the views made every morning special.The Ocean Pointe property itself is fantastic, with a beautiful heated pool, hot tub, private beach, marina, tennis and pickleball courts, and impeccably maintained grounds. It’s the perfect...
United States
Jessica F.
The price is HK$1,271
HK$3,295 total
includes taxes & fees
15 Oct - 16 Oct
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

19. 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 HK$1,870
HK$4,117 total
includes taxes & fees
14 Oct - 15 Oct
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A barbecue grill on a metal stand in a garden with palm trees and red flowers.

20. Sky Blue Escape Ocean Pointe 1314/2BA 2BR

Sky Blue Escape Ocean Pointe 1314/2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"The place was exactly as advertised and the location was perfect! Our host was very informative and provided all the details for a seamless checkin."
United States
Bryan K.
Sky Blue Escape Ocean Pointe 1314/2BA 2BR
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

Islander Resort

Islander Resort

10/10 Excellent
"Our room was very clean. Resort staff was super nice and accommodating. Amenities were nice. Pools were clean. Resort was very peaceful."
Grayson 5-night trip
Posted 13 hours ago
Islander Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Rentals information

Number of reviews
513
Accommodation
357 Condo Rentals
Lowest Price
HK$2,626
Highest Price
HK$4,117

Explore a world of travel with Expedia