Windley Key Villas - Best Villa Windley Key 2026

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Our top choices for Windley Key villas

A beachside seating area with Adirondack chairs, a fire pit, and a thatched-roof structure.

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

Key Largo

Michelle S.

includes taxes & fees

24 Sept - 25 Sept

2. Key Largo Kawama Villa L1, 3/3

Key Largo

Dayanis

includes taxes & fees

5 Oct - 6 Oct

3. Key Largo Kawama villa K1, 3/3

Key Largo

Diana

includes taxes & fees

24 Sept - 25 Sept

A resort with a central pool, multiple buildings, and a view of the ocean.

4. Beautiful Oceanside Mariner`s 3 Bedroom Townhome

Rock Harbor

Sonal G.

includes taxes & fees

24 Sept - 25 Sept

A balcony with a view of the beach and ocean, equipped with ceiling fans, outdoor furniture, and a railing.

5. Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key

Matecumbe

includes taxes & fees

13 Oct - 14 Oct

A resort with a pool, palm trees, and a view of the ocean.

6. PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key

Matecumbe

Jason B.

includes taxes & fees

27 Sept - 28 Sept

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Top Windley Key Hotel Reviews

Fisher Inn Resort & Marina

10/10 Excellent

"This place was the best place to stay I've ever been ever it is wonderful there's nothing not to like about this place the ocean the pool the people the place everybody's so nice and accommodating they will do anything they can to make sure you're happy it's paradise in paradise I would suggest to stay at this place anytime it would be a mistake not to"

Chesapeake Beach Resort

10/10 Excellent

"We had a wonderful stay at this hotel. I stayed with my mom, sister, and niece, and we truly loved the property. The location is great, the hotel is beautiful, and we really enjoyed the amenities and our time together. Overall, it was a very nice experience. The only area I feel could use some improvement is the late checkout process. I requested a late checkout until 2:00 PM because we wanted to enjoy the amenities a little longer before leaving. The property did not appear to be fully booked, so I was hoping there might be some flexibility, but unfortunately my request was not accommodated. By the time I returned to the room, packed everything, and was getting ready to leave, it was close to 1:00 PM. A member of the housekeeping staff knocked on the door and spoke to us in a way that felt rushed and unnecessarily rude, saying, “Don’t you know you were supposed to leave by 11:00 AM?” That interaction made us feel very uncomfortable and was disappointing, especially after such an enjoyable stay. I completely understand that hotels have checkout policies and that late checkout cannot always be guaranteed. However, I believe a little more flexibility when occupancy allows, along with a more courteous approach from housekeeping, would make the guest experience even better. Aside from that situation, we really loved the hotel, the location, and our stay. With a little improvement in communication and hospitality around checkout, it would be an even better experience."

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent

"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"

Amara Cay Resort

8/10 Good

"We had a great stay and overall I would definitely return as it’s a wonderful property. The hotel rooms are spacious and clean. I appreciated the responsiveness of staff and communication via text and ability to make requests via QR code. I would say breakfast was lackluster and the service was extremely slow. Furthermore, I ordered two scrambled eggs and was served powdered eggs which tasted absolutely disgusting. I send that back, and was asked if I would like “hard shell” eggs instead. I thought this was very odd! You wouldn’t expect this at a resort of this level!"

Find out more about Windley Key

Windley Key Villas information

Number of reviews	671
Accommodation	77 Villas
Lowest Price	€491
Highest Price	€3,696

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Our top choices for Windley Key villas

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

2. Key Largo Kawama Villa L1, 3/3

3. Key Largo Kawama villa K1, 3/3

4. Beautiful Oceanside Mariner`s 3 Bedroom Townhome

5. Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key

6. PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key

Find holiday rentals that suit your style

Top Windley Key Hotel Reviews

Fisher Inn Resort & Marina

Chesapeake Beach Resort

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Islander Resort

Hampton Inn Key Largo Manatee Bay

Sunset Cove Beach Resort

Amara Cay Resort

Bayside Inn Key Largo

Lime Tree Bay Resort

Find out more about Windley Key

Windley Key Villas information

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Search Villas in Windley Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windley Key villas

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

2. Key Largo Kawama Villa L1, 3/3

3. Key Largo Kawama villa K1, 3/3

4. Beautiful Oceanside Mariner`s 3 Bedroom Townhome

5. Beachfront Estate - Two Villas / Heated Pools / Docks / Dolphin & Mahi Key

6. PRIVATE BEACH / Heated Pool / Private Dock / Dolphin Key

Find holiday rentals that suit your style

Top Windley Key Hotel Reviews

Fisher Inn Resort & Marina

Find out more about Windley Key

Windley Key Villas information

Explore a world of travel with Expedia