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

Search and Rent Upper Matecumbe Key Condos

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Upper Matecumbe Key condo rentals

Beach nearby

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, (159 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
$422 nightly
The price is $459
Jul 30 - Jul 31
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed
Exterior

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)
"Beautiful condo with nice decor. We enjoyed the pool and was nice having a restaurant on site. I would definitely stay there again "
United States
Cathy
$391 nightly
The price is $425
Aug 27 - Aug 28
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
On the beach, sun loungers

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (247 reviews)
"Excellent communication with host. Proximity to pool is awesome, nice place. Lots of very good restaurants nearby. "
United States
Linda B.
$377 nightly
The price is $418
Aug 6 - Aug 7
Total with taxes and fees
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Exterior

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (35 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
$287 nightly
The price is $319
Aug 17 - Aug 18
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Beach

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.
$394 nightly
The price is $437
Aug 3 - Aug 4
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Beach nearby

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.
$408 nightly
The price is $453
Aug 11 - Aug 12
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Sun loungers, beach towels

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, (24 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
$433 nightly
The price is $481
Aug 18 - Aug 19
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
TV, offices

Ocean View Corner Penthouse Ocean Pointe 5416

Ocean View Corner Penthouse Ocean Pointe 5416
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great place - love the location! "
United States
Ann C.
$492 nightly
The price is $537
Aug 27 - Aug 28
Total with taxes and fees
Ocean View Corner Penthouse Ocean Pointe 5416
A heated pool

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.
$392 nightly
The price is $434
Aug 4 - Aug 5
Total with taxes and fees
Ocean view condo with balcony/marina view
Exterior

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
$405 nightly
The price is $440
Aug 27 - Aug 28
Total with taxes and fees
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
TV

Saltair Loft Ocean Pointe 2 BR 2 BA 1411

Saltair Loft Ocean Pointe 2 BR 2 BA 1411
Tavernier
10.0 out of 10, Exceptional, (5 reviews)
"Everything was perfect and the hosts were super helpful with recommendations for places to eat"
United States
Tricia L.
$412 nightly
The price is $447
Aug 27 - Aug 28
Total with taxes and fees
Saltair Loft Ocean Pointe 2 BR 2 BA 1411
Beach nearby

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (35 reviews)
"Loved the beach and pool."
United States
Haley P.
$410 nightly
The price is $445
Aug 24 - Aug 25
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
Beach nearby

Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Great communication. Very clean. We loved view from the room. We would definitely stay here again!"
United States
Cynthia L.
$540 nightly
The price is $589
Aug 7 - Aug 8
Total with taxes and fees
Nauti Hideaway Ocean Pointe 2314
Sun loungers

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.
$425 nightly
The price is $472
Aug 9 - Aug 10
Total with taxes and fees
Ocean Pointe - Pool, Hot Tub, View, Beach, Parking
Beach

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, (8 reviews)
"An awesome place to stay, fish and relax!"
United States
robert d.
$399 nightly
The price is $433
Aug 27 - Aug 28
Total with taxes and fees
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Beach nearby

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 with a wonderful view. It has everything you need in the kitchen. We would definitely stay there again. "
United States
Edwina S.
$406 nightly
The price is $441
Aug 27 - Aug 28
Total with taxes and fees
Ocean View Overlooking Marina Ocean Pointe 5305
TV

Ocean View Treehouse Double King Suite 3403

Ocean View Treehouse Double King Suite 3403
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Clean, comfortable and cozy! Just what we hoped for!"
Canada
Richard G.
$436 nightly
The price is $474
Aug 27 - Aug 28
Total with taxes and fees
Ocean View Treehouse Double King Suite 3403
Coffee/tea maker, fridge, microwave, oven

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

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Blue Waters
10.0 out of 10, Exceptional, (5 reviews)
"This unit was outstanding, clean, very well appointed, beautiful furnishings, significant amounts of supplies, and everything needed for a great stay. Furnishings were all new, the beds and pillows comfortable and the amenities excellent. Would definitely stay here again and recommend it to all.Thanks for a great time. Wish we could’ve stayed longer!"
United States
Mike B.
$431 nightly
The price is $469
Aug 27 - Aug 28
Total with taxes and fees
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Marina

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

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
$343 nightly
The price is $380
Aug 10 - Aug 11
Total with taxes and fees
2BR Condo w/ Ocean View, Pool & Tropical Setting
A heated pool

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great place"
United States
mike c.
$302 nightly
The price is $336
Aug 19 - Aug 20
Total with taxes and fees
OP-2 Ocean View w/heated pool beach marina
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

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"The room was very clean, and was cleaned every day during our stay. Very good breakfast with made to order eggs, omelettes and pancakes."
Angela 6-night trip
Posted 5 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Rentals information

Number of reviews
680
Accommodation
358 Condo Rentals
Lowest Price
$319
Highest Price
$589

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