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

1. Charming Home in Key Largo

Key Largo

Melinda V.

HK$2,919 total

includes taxes & fees

11 Aug - 12 Aug

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

Key Largo

"This was the perfect little home away from home! The house was perfectly clean and nice and cool! The AC in the bedroom was fantastic and kept the room a perfect temperature for sleeping. In addition the bed was super comfortable! We had a great time in the campground and were so excited about the kayaks available for our use. We have already recommended this house and the campground to our friends and family and can’t wait to come and stay again soon!"

Carrie D.

HK$2,159 total

includes taxes & fees

24 Aug - 25 Aug

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

3. Little Peace of Haven

Key Largo

Mitchel R.

HK$3,292 total

includes taxes & fees

7 Sept - 8 Sept

4. Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo

Michelle S.

HK$4,586 total

includes taxes & fees

20 Aug - 21 Aug

5. Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Key Largo

"We had a wonderful stay at this RV over July 4th weekend in Key Largo. The location was perfect exactly what we were looking for. Everything about the property made for a great family getaway.Communication was a little confusing at first — it seemed like a different number was reaching out initially, and when I replied to that one, I didn’t hear back. Once I was in touch with the host’s actual number, though, communication was reliable. By that point we’d already figured out the answers to our...

Jennifer A.

6. Sunrise Escape - Ocean Front Villa - Sleeps 10

Key Largo

Tracey C.

HK$5,937 total

includes taxes & fees

9 Aug - 10 Aug

7. Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Key Largo

Jason C.

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

Key Largo

Dave B.

HK$2,763 total

includes taxes & fees

26 Aug - 27 Aug

9. 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.

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

Key Largo

Ann

Coffee/tea maker, fridge, microwave, oven

11. New Cozy getaway on waterfront in Key Largo! Bring your own boat!

Cross Key Waterways

Kim C.

HK$3,416 total

includes taxes & fees

21 Aug - 22 Aug

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

Key Largo

Susan S.

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

Key Largo

Tom W.

HK$4,856 total

includes taxes & fees

10 Aug - 11 Aug

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

Key Largo

Teresa H.

HK$4,314 total

includes taxes & fees

2 Sept - 3 Sept

15. Key largo Kawama Villa N2

Key Largo

Georgi T.

16. New Oceanside Paradise with Pool and Waterfront Views!

Key Largo

Ravone L.

HK$13,541 total

includes taxes & fees

5 Sept - 6 Sept

17. Waterfront / Ocean Access Canal / Kamp Key / Homes

Matecumbe

"Excellent house. Very clean. We had a little trouble with the check in code and we were immediately contacted and the code was changed and we were in within minutes. The maintenance guy stopped by to make sure we got in and everything was good. EXCELLENT Customer Service!!!!!House was very well stocked with pots and pans and misc things needed for a week stay! Right on a nice little canal with plenty of room for our boat."

Mike H.

HK$7,187 total

includes taxes & fees

8 Sept - 9 Sept

18. Waterfront Cottage - Beach and Dockage! Open Water Views!

Key Largo

Shane F.

HK$4,626 total

includes taxes & fees

19 Aug - 20 Aug

19. Oceanside Kawama Villa R5

Key Largo

Kenny C.

HK$4,912 total

includes taxes & fees

9 Aug - 10 Aug

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

20. Two Authentic Conch Houses with Private Beach on FL BAY

Tavernier

Tracie H.

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Top Windley Key Hotel Reviews

Lime Tree Bay Resort

10/10 Excellent

"Very nice stay at the Keys"

Hampton Inn Key Largo Manatee Bay

10/10 Excellent

"Please note, I am rating our stay 5 stars because we had a wonderful fun time at this hotel. The front desk lady (on the left when you face the front desk) was so very helpful and accommodating (sorry, didn't get her name). We were appointed a room that met our needs, first floor, garden view to the pool and very close to the beach. The little beach was delightful and we made great use of the noodles, kayaks and floats. Breakfast was not only free but awesome! Everyday eggs made a different way, meat variety and potatoes. In addition breads, muffins, cereals, yogurt, juices, milk and of course those yummy waffles. The landscape is lush and tropical, we enjoyed that very much. There are a few things that could improve such as those out of date super firm mattresses, I thought no hotels especially Hilton would have those around anymore. Now, this one is important, more umbrellas are desperately needed in the pool area, at least 3 on each row of lounge chairs. The pool is beautiful and refreshing but can't hang around under the Florida sun for long. We will return to this hotel!"

Chesapeake Beach Resort

8/10 Good

"The ocean view suite had a spectacular view of the basin and ocean. The location is in the middle of everything. The grounds have many private spots right on the ocean. The on site Tiki bar was enjoyable and on Sat there was a live entertainer who was very good. The pools were nice but would be better if cooled. They are remodeling and it was very loud when we arrived on Fri. The associate at the front desk, Jasmine, was professional, responsive, and friendly. She investigated and texted us to let us know it would stop by 5p and not continue until Monday. The room didn't have towel rods or hooks and no wall art. Felt recently remodeled without final touches. These are the only reasons I didn't give it a 5. I would go back."

Sunset Cove Beach Resort

10/10 Excellent

"We had #10. Greta view, quiet, clean, full kitchen, great AC nice shower. FREE water activities, snorkel, swim, float. Shaded tables plenty of chairs in the sun. Coffee AND served was nice 2 full service restaurants Bayside & GiGorgeios within 3-5 min walking distance. Live music. Another local spot across the street for great fairly priced breakfast. John Pennecamp state park just up the street. Nice, but book snorkel or boat trips elsewhere. Booze Cruse for those who like that are pet friendly. All in al very nice no complaints. Book this place."

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