Windley Key Vacation Homes

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 holiday homes

2 bedrooms, iron/ironing board, WiFi, bed sheets

1. Little Peace of Haven

Key Largo

Mitchel R.

HK$3,314 total

includes taxes & fees

1 Sept - 2 Sept

2. Charming Home in Key Largo

Key Largo

Melinda V.

HK$2,854 total

includes taxes & fees

2 Sept - 3 Sept

Beach nearby, sun-loungers, beach towels

3. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Key Largo

Aaron G.

4. Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Key Largo

Kevin M.

HK$2,211 total

includes taxes & fees

1 Sept - 2 Sept

5. Sunrise Escape - Ocean Front Villa - Sleeps 10

Key Largo

Lauren S.

HK$5,827 total

includes taxes & fees

1 Sept - 2 Sept

6. Key Largo Kawama Villa L1, 3/3

Key Largo

Dayanis

HK$4,456 total

includes taxes & fees

1 Sept - 2 Sept

7. New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

Key Largo

Teresa H.

HK$3,470 total

includes taxes & fees

1 Sept - 2 Sept

8. Oceanside Retreat w/Rooftop, Pool & Kayaks

Key Largo

HK$5,824 total

includes taxes & fees

9 Sept - 10 Sept

9. NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Key Largo

Tom W.

HK$4,814 total

includes taxes & fees

1 Sept - 2 Sept

10. Oceanside Kawama Villa R5

Key Largo

Anonymous traveller

HK$4,886 total

includes taxes & fees

1 Sept - 2 Sept

11. Key Largo Villa, Kawama K5, 3/3

Key Largo

Susan S.

HK$4,715 total

includes taxes & fees

1 Sept - 2 Sept

Coffee/tea maker, fridge, microwave, oven

12. New Oceanside Paradise with Pool and Waterfront Views!

Key Largo

Ravone L.

HK$6,644 total

includes taxes & fees

1 Sept - 2 Sept

13. Waterfront Tiny Home w/ Pool, Beach, Dock, Kayaks

Key Largo

Dave B.

HK$2,506 total

includes taxes & fees

15 Sept - 16 Sept

14. Waterfront Tiny House w Pool, Beach, and Boat Dock

Key Largo

Ann

HK$2,698 total

includes taxes & fees

1 Oct - 2 Oct

15. Kawama L4 - Upscale Oceanside Villa with Marina

Key Largo

Kim W.

HK$4,475 total

includes taxes & fees

1 Sept - 2 Sept

16. Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Key Largo

Barbara A K.

HK$3,071 total

includes taxes & fees

14 Sept - 15 Sept

17. New Tiny Home-Paddle Boards, Kayaks, Pool, Marina

Key Largo

"Tiny HomeThis tiny home was comfortable, clean, and fully stocked with all you need to vacation in the Keys! At first, I was hesitant on booking a tiny home coming from a 3,200sqft house but we found the layout functional and actually cozy with good amounts of space.I would recommend the place along with the property management team who ensured all communications were answered quickly and thoroughly!Would stay here again!"

Christina R.

HK$2,307 total

includes taxes & fees

2 Sept - 3 Sept

1 bedroom, desk, iron/ironing board, travel cot

18. Tranquility Bungalow at Largo Resort

Key Largo

Becky M.

HK$3,661 total

includes taxes & fees

14 Sept - 15 Sept

19. Serenity Bungalow at Largo Resort

Key Largo

Kimberly V.

HK$3,638 total

includes taxes & fees

2 Sept - 3 Sept

20. El Encanto

Key Largo

HK$5,001 total

includes taxes & fees

2 Sept - 3 Sept

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Top Windley Key Hotel Reviews

Cheeca Lodge & Spa

8/10 Good

"Amenities and the property are absolutely beautiful. Mixed feelings about the staff. The bartenders and pool waitress get an A+. Everyone else could be friendlier :) No problems getting through the gate, which I've had issues with at other properties. Even when the night guard steps away, they will send security in less than a minute to open the gate for you so that was great. We enjoyed our stay and I would go back."

Amara Cay Resort

8/10 Good

"The resort is great! I did, however, leave behind my bathing suit and a personal towel hanging on the back of the bathroom door. When I called three days later after realizing they were missing, I learned that housekeeping had set the items aside. I was surprised that no one had contacted me to let me know they had been found. The front desk explained that I would need to provide a prepaid shipping label, which I promptly emailed. I asked for confirmation that the label had been received but received no response. After several days, I followed up again and still heard nothing. My items were eventually returned, and I’m grateful for that. Overall, I had a nice stay, but the lack of communication was disappointing. A more attentive, customer-focused team would have notified me that the items had been found and acknowledged receipt of the shipping label—especially after multiple messages. A little follow-through and basic courtesy would have made a significant difference."

Islander Resort

8/10 Good

"Great property with an amazing concept, especially in an area where there aren’t many high-end properties offering this style and experience. The facilities are excellent, and overall we really enjoyed our stay. My only negative feedback is that a few members of staff were constantly on their phones watching clips and videos, often with the volume turned up. We found this quite annoying, particularly when trying to relax quietly by the pool. It would be great if staff could be reminded to use headphones or keep phone use to a minimum in guest relaxation areas. Room maintaince could also be better."

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