Holiday Rentals Windley Key from ฿3,198: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Windley Key holiday rentals

25-inch flat-screen TV with digital channels, TV

1. Treasure Harbor

Islamorada

Molly

฿8,363 total

includes taxes & fees

22 Sept - 23 Sept

2. Breezy Palms Resort

Matecumbe

Dionisio

฿3,198 total

includes taxes & fees

30 Sept - 1 Oct

Private beach, sun-loungers, beach umbrellas, beach towels

3. Island Bay Resort

Tavernier

Katie Lyn

฿7,515 total

includes taxes & fees

29 Sept - 30 Sept

4. Kings Kamp

Key Largo

Michelle

฿7,557 total

includes taxes & fees

22 Sept - 23 Sept

5. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Matecumbe

฿84,293 total

includes taxes & fees

14 Oct - 15 Oct

6. Premium Floating Bungalow by Stay Ombi

Key Largo

Deivys

฿30,844 total

includes taxes & fees

22 Sept - 23 Sept

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Top Windley Key Hotel Reviews

Islander Resort

10/10 Excellent

"Perferto"

Waterside Suites & Marina

8/10 Good

"We stayed for three nights in a two-bedroom suite. For the price, the stay was reasonable, and there were definitely some positives. The suite was spacious, the bedding was clean and good quality, the beds and pillows were comfortable, and we had a nice view of the canal. Free parking was also a big plus — we had three cars in our group and received parking passes for all of them. However, there are quite a few details that could be improved. The suite was booked for four guests but was not really equipped for four: there were not enough dishes, chairs, or towels, and even the coffee maker was missing filters. The outdoor and BBQ areas looked somewhat dated and poorly maintained, the ice machines were not working, and the pool could have been better maintained. We also did not receive any housekeeping or check-ins during our three-day stay. Our room faced the restaurant across the canal, so weekend evenings were quite noisy. The canal view is nice, but if you are looking for peace and privacy, keep this in mind. Overall, considering the price, our stay was acceptable. If you are coming with a group or celebrating a special occasion and plan to cook, I would recommend bringing some of your own kitchen supplies. We came prepared and were able to enjoy our stay despite the shortcomings."

Chesapeake Beach Resort

8/10 Good

"They do strive to provide great customer service and promised to have clean rooms but there were some minor things I noticed after the staff assured me they pay attention to great detail. The wall in bathroom had some mysterious staining and the toilet seat was super loose on the verge of falling off. Overall, this hotel was by far the one of the better ones around and had a professional and friendly staff. We stayed here because the hotel we booked initially down the road had bugs in the bed, so it was a relief to stay here last minute as a backup without the pests."

Sunset Cove Beach Resort

10/10 Excellent

"I was very impressed with the property. It exceeded my expectations.I will definitely come back and stay here again. The nicest lady checked us in. She went on to make sure everything was perfect for us. I’m upset that I can not rember her name so she can get credit for being so kind and welcoming."

Cheeca Lodge & Spa

10/10 Excellent

"Loved the room, quiet vibe, designated parking, the water front area, and staff. Nice surrounding area. You need a car if you want to go to Key West or nearby cities. If you want activity recommend planning ahead. We were celebrating wedding anniversary and this fit the bill. Loved it and would come back. Things to be mindful of. Yes there is a resort fee and the property holds a fee per day for Incidentals. Having the ability to know it was negotiable would have been better than finding out when I checked out. Adult pool only was nice and relaxing. The other pools were nice but very lively, if you want to chill the other pools may not be your thing. We wanted to go to a night club with dancing but there were none in this area near the resort. We went to Hog heaven, live music was great but not a night club. The Cheeca Lodge and Spa was wonderful!"

Fisher Inn Resort & Marina

10/10 Excellent

"Clean and comfortable rooms. I love the location relative to things to do in the Keys. We used the bikes while there and have used kayak/paddleboards in past. The staff is absolutely amazing. I had messed up the dates of the reservation. Jamal worked really hard to get me a room at a rate i could afford. REALLY appreciate his efforts. We'll stay here again on our next trip to Islamorada"

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Check prices for these dates

Our top choices for Windley Key holiday rentals

1. Treasure Harbor

2. Breezy Palms Resort

3. Island Bay Resort

4. Kings Kamp

5. Beach Residence Private Overwater Dock Heated Pool Mahi Key

6. Premium Floating Bungalow by Stay Ombi

Find holiday rentals that suit your style

Top Windley Key Hotel Reviews

Islander Resort

Reefhouse Resort & Marina

Waterside Suites & Marina

Chesapeake Beach Resort

Sunset Cove Beach Resort

Cheeca Lodge & Spa

Lime Tree Bay Resort

Rock Reef Resort

Fisher Inn Resort & Marina

Find out more about Windley Key

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Search Holiday Rentals in Windley Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windley Key holiday rentals

1. Treasure Harbor

2. Breezy Palms Resort

3. Island Bay Resort

4. Kings Kamp

5. Beach Residence Private Overwater Dock Heated Pool Mahi Key

6. Premium Floating Bungalow by Stay Ombi

Find holiday rentals that suit your style

Top Windley Key Hotel Reviews

Islander Resort

Find out more about Windley Key

Go further with the Expedia app