A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Windley 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 ￥12,737
￥48,004 total
includes taxes & fees
Oct 18 - Oct 19
Florida Keys Getaway - Slps 4 - Ocean View
A resort with multiple buildings, a swimming pool, tennis courts, and a view of the ocean.

2. 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 ￥24,447
￥67,429 total
includes taxes & fees
Oct 22 - Oct 23
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
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, (115 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is ￥20,550
￥58,213 total
includes taxes & fees
Oct 26 - Oct 27
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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, (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 ￥19,763
￥56,542 total
includes taxes & fees
Oct 19 - Oct 20
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.

5. 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 ￥21,344
￥54,447 total
includes taxes & fees
Oct 17 - Oct 18
Amazing Ocean view condo
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 ￥23,657
￥66,340 total
includes taxes & fees
Oct 17 - Oct 18
Reel Key Largo Escape Ocean Pointe 5209
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

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.
The price is ￥24,450
￥67,437 total
includes taxes & fees
Oct 17 - Oct 18
Blue Haven Key Largo | Ocean Pointe 1315
Beach

8. 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 ￥22,866
￥65,249 total
includes taxes & fees
Oct 17 - Oct 18
Aqua Vista Ocean Pointe 3307
A pool area with a palm tree, a showerhead, and blue lounge chairs.

9. 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 ￥29,881
￥54,034 total
includes taxes & fees
Oct 25 - Oct 26
Ocean Pointe Ocean View w/heated pool beach marina
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

10. 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 ￥21,288
￥63,109 total
includes taxes & fees
Nov 16 - Nov 17
Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
Marina

11. Friends' Getaway 1BR w/ Ocean View, Pool & Beach

Friends' Getaway 1BR w/ Ocean View, Pool & Beach
Tavernier
The price is ￥15,821
￥55,679 total
includes taxes & fees
Oct 28 - Oct 29
Friends' Getaway 1BR w/ Ocean View, Pool & Beach
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

12. 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 ￥36,042
￥80,784 total
includes taxes & fees
Oct 25 - Oct 26
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A beachside resort with a thatched umbrella, palm trees, and a dock.

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.
The price is ￥26,980
￥71,210 total
includes taxes & fees
Oct 18 - Oct 19
Lazy Daze Double King Suite Ocean Pointe 2310
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 ￥26,980
￥70,736 total
includes taxes & fees
Nov 1 - Nov 2
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Pool

15. 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, (11 reviews)
"Clean and perfect location"
United States
Joanne P.
The price is ￥25,399
￥69,188 total
includes taxes & fees
Oct 18 - Oct 19
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
A hotel room with a bed, a wicker chest of drawers, a white door, and a framed picture on the wall.

16. 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 ￥27,928
￥72,359 total
includes taxes & fees
Oct 18 - Oct 19
Marina and Ocean View, 2 Bed, 2 Bath End Unit 4201
Beach

17. 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 ￥28,403
￥70,201 total
includes taxes & fees
Nov 1 - Nov 2
3212 Across from Pool * King & Queen/Twin Bunk Bed
A modern showerhead with multiple water streams, a tiled wall, and a pool area with blue chairs and a palm tree.

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 ￥28,173
￥63,077 total
includes taxes & fees
Oct 17 - Oct 18
Ocean view condo with balcony/marina view
A beach with thatched umbrellas, lounge chairs, and palm trees.

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

Coastal Retreat, Pool, Marina, Ocean View, FL Keys
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"The Perfect Coastal Getaway!We had an amazing weekend stay! The apartment is in the perfect location at the beginning of the Keys, with shops conveniently nearby. From the moment we arrived, we felt like we were in a true coastal retreat—the apartment was spotless, beautifully organized, cozy, and equipped with everything we needed to cook, relax, and enjoy quality family time.Honestly, we didn’t even need to leave the complex! The amenities were fantastic, with a beautiful pool and bar, a small...
United States
Manuel S.
The price is ￥25,612
￥66,383 total
includes taxes & fees
Oct 21 - Oct 22
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
A beach with lounge chairs, a thatched umbrella, and palm trees.

20. 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.
The price is ￥26,189
￥67,908 total
includes taxes & fees
Nov 16 - Nov 17
Ocean View Overlooking Marina Ocean Pointe 5305
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
"Great location"
Dianne 5-night trip
Posted 1 hour ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Condo Rentals information

Number of reviews
535
Accommodation
374 Condo Rentals
Lowest Price
￥48,004
Highest Price
￥80,784

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