Search and Rent Windley Key Condos

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Windley Key condo rentals

Pool
Amazing Ocean view condo

Condo in Tavernier

Amazing Ocean view condo
9.6 out of 10, Exceptional, (42)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
$342 nightly
The price is $380
Jan 19 - Jan 20, 2026
Total with taxes and fees
Amazing Ocean view condo
A heated pool
Serenity In The Sun Condo Fabulous Ocean View

Condo in Tavernier

Serenity In The Sun Condo Fabulous Ocean View
10.0 out of 10, Exceptional, (108)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$417 nightly
The price is $464
Jan 5 - Jan 6, 2026
Total with taxes and fees
Serenity In The Sun Condo Fabulous Ocean View
Pool
Blue Haven Key Largo | Ocean Pointe 1315

Condo in Tavernier

Blue Haven Key Largo | Ocean Pointe 1315
9.6 out of 10, Exceptional, (15)
"This condo was everything we needed. Lots of space, bug comfy beds, hreat shower and the pool at the complex was great in the late afternoon after a day exploring the upper keys. There were works going on at the conplex when we were there which took the edge off things as 9am drilling on Monday morning wasnt welcome but I only knocked 1 star off - otherwise wouldnt hesitate to recommend!"
United Kingdom
Philippa
$392 nightly
The price is $426
Jan 21 - Jan 22, 2026
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315
Pool
Modern and Coastal Ocean Pointe 2307

Condo in Tavernier

Modern and Coastal Ocean Pointe 2307
10.0 out of 10, Exceptional, (122)
"We enjoyed our stay!"
United States
Halley R.
$391 nightly
The price is $424
Jan 15 - Jan 16, 2026
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307
Pool
Flamingo Flats Ocean Pointe 5306 2BR/2BA

Condo in Tavernier

Flamingo Flats Ocean Pointe 5306 2BR/2BA
9.6 out of 10, Exceptional, (7)
"Great location and prompt support with all questions we had. "
United States
Jim I.
$389 nightly
The price is $423
Jan 14 - Jan 15, 2026
Total with taxes and fees
Flamingo Flats Ocean Pointe 5306 2BR/2BA
Terrace/patio
Ocean view condo with balcony/marina view

Condo in Tavernier

Ocean view condo with balcony/marina view
8.8 out of 10, Excellent, (42)
"The condo was renovated, and very nicely decorated, very clean and cozy. We enjoyed our short stay. Community and pool were good too. "
United States
Lina
$385 nightly
The price is $427
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ocean view condo with balcony/marina view
Pool
Sea View Farm Style Ocean front Condo Views

Condo in Tavernier

Sea View Farm Style Ocean front Condo Views
10.0 out of 10, Exceptional, (155)
"The property was excellent."
United States
June M.
$401 nightly
The price is $446
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sea View Farm Style Ocean front Condo Views
Pool
Lazy Daze Double King Suite Ocean Pointe 2310

Condo in Tavernier

Lazy Daze Double King Suite Ocean Pointe 2310
9.8 out of 10, Exceptional, (26)
"Everything was exceptionally nice. Would definitely book again."
United States
Sharon
$403 nightly
The price is $438
Jan 13 - Jan 14, 2026
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
Pool
Captains Quarters Ocean Pointe 4405

Condo in Tavernier

Captains Quarters Ocean Pointe 4405
10.0 out of 10, Exceptional, (13)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
$423 nightly
The price is $460
Jan 12 - Jan 13, 2026
Total with taxes and fees
Captains Quarters Ocean Pointe 4405
Pool
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Condo in Tavernier

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."
United States
Kevin W.
$435 nightly
The price is $474
Jan 14 - Jan 15, 2026
Total with taxes and fees
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Marina
Family 2BR w/ Ocean Views, Pool & Beach Access

Condo in Tavernier

Family 2BR w/ Ocean Views, Pool & Beach Access
2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice and clean accommodation conveniently located to several restaurants. Nice place to relax. The pier and beach are a nice bonus. "
United States
Issam T.
$451 nightly
The price is $500
Jan 13 - Jan 14, 2026
Total with taxes and fees
Family 2BR w/ Ocean Views, Pool & Beach Access
Beach nearby
Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR

Condo in Tavernier

Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR
9.4 out of 10, Exceptional, (48)
"clean great location "
United States
Tracey A.
Oceanfront Views at Ocean Pointe + Pool + Beach & Marina Access, Updated 2BR
Pool
Aqua Vista Ocean Pointe 3307

Condo in Tavernier

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."
United States
Michelle
$423 nightly
The price is $460
Jan 4 - Jan 5, 2026
Total with taxes and fees
Aqua Vista Ocean Pointe 3307
Beach nearby
Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities

Condo in Blue Waters

Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities
9.4 out of 10, Exceptional, (24)
"Unit was everything we hoped for, building was nice, quiet, and had good amenities, and the grounds and pool were great. Would absolutely stay here again on future trips."
United States
Jacob W.
$668 nightly
The price is $743
Jan 8 - Jan 9, 2026
Total with taxes and fees
Ocean Pointe 2BR Retreat Ocean View, Pool, Marina & Resort Amenities
Pool
Ocean View Overlooking Marina Ocean Pointe 5305

Condo in Tavernier

Ocean View Overlooking Marina Ocean Pointe 5305
10.0 out of 10, Exceptional, (24)
"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."
United States
Donald
$427 nightly
The price is $465
Jan 27 - Jan 28, 2026
Total with taxes and fees
Ocean View Overlooking Marina Ocean Pointe 5305
Pool
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Condo in Tavernier

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
9.8 out of 10, Exceptional, (26)
"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). "
United States
Jenny G.
$385 nightly
The price is $418
Jan 28 - Jan 29, 2026
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Property grounds
Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys

Condo in Tavernier

Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys
9.8 out of 10, Exceptional, (162)
"place was great. wish the price of using the dock would be known before I booked it,"
United States
Duffy P.
$575 nightly
The price is $638
Jan 13 - Jan 14, 2026
Total with taxes and fees
Ocean Front 2/2 Condo,OCEAN FRONT/MARINA VIEW,Tavernier/Key Largo Fl. Fla.Keys
Sun loungers, beach towels
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Condo in Tavernier

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
10.0 out of 10, Exceptional, (12)
"Perfect Stay."
United States
suhaela s.
$515 nightly
The price is $572
Jan 4 - Jan 5, 2026
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Terrace/patio
Toes in the Sand - 2 Bedroom Condo Sleeps 4

Condo in Tavernier

Toes in the Sand - 2 Bedroom Condo Sleeps 4
10.0 out of 10, Exceptional, (28)
"The room was beautiful as was the view. We had a great time utilizing the game area. The pool was nice and clean and the food there was amazing. Would definitely recommend!!"
United States
Jacob F.
$413 nightly
The price is $459
Jan 7 - Jan 8, 2026
Total with taxes and fees
Toes in the Sand - 2 Bedroom Condo Sleeps 4
Beach
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

Condo in Blue Waters

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
2.0 star property
10.0 out of 10, Exceptional, (2)
"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! "
United States
Peter A. Z.
$448 nightly
The price is $487
Jan 13 - Jan 14, 2026
Total with taxes and fees
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
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 Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return."
Julie 2-night trip
Posted 10 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Condo Rentals information

Number of reviews
805
Accommodation
417 Condo Rentals
Lowest Price
$380
Highest Price
$743

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