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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Browse Select Windley Key Condo Rentals

Topsider Resort
Dock

Topsider Resort

3.5 star property
8.8 out of 10, Excellent, (61)
"Its a great choice for small families looking to relax. Heated pool and hot tub. on property beach access (gulf side). Kayaks and bikes to use. inside the dwelling, master bedroom w/ full bath, another bedroom w/ two twin beds, another full bath, full kitchen + kitchenette, and living room. Really pleased. "
Topsider Resort
End Unit With Ocean Views And Juliet Balcony. 2 Bedroom Condo by RedAwning
Condo, 2 Bedrooms | Property grounds

End Unit With Ocean Views And Juliet Balcony. 2 Bedroom Condo by RedAwning

3.0 star property
End Unit With Ocean Views And Juliet Balcony. 2 Bedroom Condo by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windley Key

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (459)
"Expedia let me down. I ordered a room with two beds, and when we arrived, they gave me a room with a king bed. We are two hetero men on a fishing trip, and we were not really wanting to share a bed. BP blamed it on Expedia and said they couldn't give me a different room and said they didn't have another room with two beds to give us anyway. They did give us a roll-away bed, but the couch was more comfortable! We toughed it out in the King bad, but that was a bad start to the stay! "
The price is ₹10,516
₹16,260 total
includes taxes & fees
21 May - 22 May
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (58)
"Everything was perfect. Every detail has been thought of. The rooms were immaculate and so well decorated. The property is really well maintained. We loved all of the games around the resort as well. Highly recommend! "
The price is ₹45,401
₹55,777 total
includes taxes & fees
5 May - 6 May
The Islands of Islamorada
Key Largo Cottages
Beach/ocean view

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
Key Largo Cottages
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.