Windley Key Condo Rentals

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

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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

Tavernier

Nick

HK$2,608 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a large TV, a white coffee table, and a balcony with a view of the ocean.

2. Corner Penthouse | Ocean Views | Ocean Pointe 5416

Tavernier

Ann C.

HK$4,309 total

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a sofa, a flat-screen TV, a ceiling fan, and a view of the outdoors.

3. Sunshine Paradise | Ocean View | Ocean Pointe 4402

Tavernier

Luella K.

HK$3,530 total

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

4. Coral Penthouse | Corner Unit | Ocean Pointe 4216

Tavernier

David C.

HK$3,448 total

includes taxes & fees

25 Oct - 26 Oct

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

Tavernier

Jerad E.

HK$2,724 total

includes taxes & fees

29 Oct - 30 Oct

A beachside lounge with a thatched roof, a wooden bench, and a view of the sea and greenery.

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

Tavernier

Pam K.

7. Sunrise Penthouse | 1BR 2BA | Ocean Pointe 3316

Tavernier

Chris

HK$3,152 total

includes taxes & fees

31 Oct - 1 Nov

A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

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

Tavernier

Les

HK$2,861 total

includes taxes & fees

25 Oct - 26 Oct

A room with a view of the ocean, a balcony with a railing, and a table with a white box.

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

Tavernier

Joanne P.

HK$3,359 total

includes taxes & fees

31 Oct - 1 Nov

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

Tavernier

Aaron H.

HK$3,527 total

includes taxes & fees

31 Oct - 1 Nov

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

Tavernier

Mary Katherine B.

HK$2,727 total

includes taxes & fees

27 Oct - 28 Oct

A room with a large window overlooking a beach and a thatched structure.

12. Marina & Ocean | Corner Unit | Ocean Pointe 4201

Tavernier

"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...

Cara B.

HK$3,589 total

includes taxes & fees

30 Oct - 31 Oct

A balcony with a view of a green landscape, a potted plant, and a chair.

13. Sky Blue Escape | Ocean View | Ocean Pointe 1314

Tavernier

Bryan K.

HK$3,439 total

includes taxes & fees

25 Oct - 26 Oct

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a gazebo.

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

Tavernier

HK$3,503 total

includes taxes & fees

24 Nov - 25 Nov

15. Starfish Seas | Ocean View | Ocean Pointe 1302

Tavernier

Miranda J.

HK$3,532 total

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a large window, a ceiling fan, a sofa, two armchairs, a coffee table, and a side table with lamps.

16. Lazy Daze | Double King Suite | Ocean Pointe 2310

Tavernier

Haley P.

A wooden pier leading to a thatched-roof structure with outdoor seating.

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

Tavernier

Justin D.

HK$3,009 total

includes taxes & fees

25 Oct - 26 Oct

A beachside lounge with lounge chairs and a wooden deck overlooking the ocean.

18. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Tavernier

Alicia

HK$4,105 total

includes taxes & fees

3 Nov - 4 Nov

A beachside resort with palm trees, thatched umbrellas, and lounge chairs.

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

Tavernier

"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...

Manuel S.

HK$3,366 total

includes taxes & fees

25 Oct - 26 Oct

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

Tavernier

Rodney B.

HK$3,366 total

includes taxes & fees

26 Oct - 27 Oct

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Top Windley Key Hotel Reviews

Bayside Inn Key Largo

10/10 Excellent

"Had a great vacation here with my wife. Good amenities and Good food next door."

Amara Cay Resort

10/10 Excellent

"We had a great stay here. The front desk staff greeted us with genuine warmth and made the check-in process completely seamless. The room was spotless, quiet, and very comfortable. The housekeeping team worked had to keep everything fresh and well-maintained. The bed was comfortable, and the bathroom had a great shower with quality toiletries. The range of amenities really stood out, from the reliable high-speed Wi-Fi and well-equipped fitness center to the breakfast options available in the morning. We would happily stay here again!"

Waterside Suites & Marina

8/10 Good

"The room was clean and grounds kept nice. Kitchenette - I wish there were better utensils to cook with. The bed was very firm - we sleep on a firm mattress at home, but this was a very firm mattress. Good location and the patio is nice. Didn't even realize there was a pool until the last day we were here."

Hampton Inn Key Largo Manatee Bay

10/10 Excellent

"The staff were wonderful, especially Jolene. The first impression is this hotel needs some TLC. The hotel is going through a renovation, which will be great, but it has so much character now. I ended up loving this quirky hotel. We stayed twice - first we had a room not renovated and second a room that was renovated. The little beach is nice - some people there saw Manatees, but we weren't so lucky. The landscaping in the courtyard is very nice and we were greeted with Iguanas and Ibis, which was fun. The pool looked very inviting and many guests were using it. I'd love to have an opportunity to come back to this hotel."

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent

"I stayed in a two bed suite in early October loved it . It was spacious had the balcony beautiful blue water view. Love that it’s pet friendly, you can take your boat to dock there but unfortunately there is no boat launching or trailer storage . Other than that the beach was awesome prefer it better than the pool . Their restaurants are nice liked all their food I would recommend to come and stay you’ll like it"

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