Find hotels in Windley Key, FL from CA $183

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Top 10 Windley Key hotels and places to stay

Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC
Towels
Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC
9.8 out of 10, Exceptional, (8)
"Excellent location if you're looking for safe, quiet, very clean complex. Everyone was very nice. Our unit was very nice and the back patio so relaxing. Would definitely recommend!"
Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC
Palm Villa May dates available
Outdoor pool
Palm Villa May dates available
9.8 out of 10, Exceptional, (123)
"The owners are 5 star! The villa is conveniently located to the main Hawks Cay lodge as well as the Angler & Ale Restaurant and docks. The unit is clean, comfortable and accommodates 4 adults with everything you need for a relaxing, fun filled getaway. If you plan ahead, like we always do when coming to the Keys, I suggest you stop at Publix and stock up on any food, drinks and extras (shampoo, laundry detergent, dishwasher tabs, etc) that you may want while on property as it’s about a 25 min...
Palm Villa May dates available
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
Beach
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
9.8 out of 10, Exceptional, (42)
"Love Duck Key!"
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
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Villa 5054 on Duck Key BOAT SLIP available
Property grounds
Villa 5054 on Duck Key BOAT SLIP available
9.8 out of 10, Exceptional, (36)
"My husband and I traveled with our son (6) for our first Keys trip the first week of April. The rental was comfortable with a full kitchen for our own cooking and everything was clean. The view is perfection and the deck is steps away from the water. We were able to fish and enjoy the beautiful sunsets right outside the place. The location is quiet enough with alot of families but close to shops and restaurants. We will definitely be back and Frank was easy to contact. Great adventure!"
The price is CA $326
CA $799 total
includes taxes & fees
May 20 - May 21
Villa 5054 on Duck Key BOAT SLIP available
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
Property grounds
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
9.8 out of 10, Exceptional, (55)
"Enjoyed the location everyone at this location was very friendly, the views and sunrises were beautiful. The unit could use a new mattress but enjoyed the stay."
Fully furnished studio, 50 yards from ocean, shared pool, fishing-jetty
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
The Islands of Islamorada
4.0 star property
9.6 out of 10, Exceptional, (35)
"My wife and I have been traveling to Islandmorada for many years and this place is what we have been searching for. Clean, quaint, all the amenities of a large restort withiut the corporation feel. Absolutely refreshing!"
The Islands of Islamorada
2-BEDROOM 3 BATH 299nt + Pool on BLUE LAGOON. SLEEPS 6
Pool
2-BEDROOM 3 BATH 299nt + Pool on BLUE LAGOON. SLEEPS 6
9.6 out of 10, Exceptional, (32)
"Great property, excellent location, very well maintained. Enjoyed our stay, Marc was very easy to work with, excellent communication and very responsive. My only criticism is the bathrooms are a bit small, but everything else was perfect."
2-BEDROOM 3 BATH 299nt + Pool on BLUE LAGOON. SLEEPS 6
Grassy Flats Resort & Beach Club
Exterior
Grassy Flats Resort & Beach Club
2.5 star property
9.4 out of 10, Exceptional, (160)
"Super friendly and helpful staff. Great location for just chilling out. Green - refill water bottles provided. Our double aspect room in the adult only part of the hotel was stunning and had the quietest air-con that didn't disturb my sleep - the refrigerator still rumbled away in the night but was quietest of all the others on our road trip!! (not used to air con or a refrigerator in the bedroom at home!!)"
The price is CA $459
CA $516 total
includes taxes & fees
May 28 - May 29
Grassy Flats Resort & Beach Club
Casa Morada
Property grounds
Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (350)
"Loved our stay! Unique property, we will be back again! Thank you!"
The price is CA $401
CA $669 total
includes taxes & fees
May 27 - May 28
Casa Morada
Villa 5023 on Duck Key BOAT SLIP available
Fridge, microwave, oven, stovetop
Villa 5023 on Duck Key BOAT SLIP available
9.4 out of 10, Exceptional, (25)
"This unit was spotless and laid out in a very efficient way. The views from the back porch and upper porch off the bedroom are gorgeous, especially for sunsets. The stairs to the bedrooms on the upper level are high however, for people that have trouble with stairs, it could be difficult. We loved the cleanliness and the location, which was close to Marathon and restaurants."
The price is CA $326
CA $799 total
includes taxes & fees
May 20 - May 21
Villa 5023 on Duck Key BOAT SLIP available
Sunset Inn
Outdoor pool, free cabanas
Sunset Inn
3.0 star property
9.2 out of 10, Wonderful, (1000)
"Great place! Would stay again "
The price is CA $195
CA $233 total
includes taxes & fees
May 16 - May 17
Sunset Inn
Pines & Palms Resort
Outdoor pool, a heated pool, pool umbrellas, sun loungers
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (955)
"Beautiful place to get away with your family"
The price is CA $231
CA $324 total
includes taxes & fees
Jun 6 - Jun 7
Pines & Palms Resort
Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1005)
"Beautiful property"
The price is CA $436
CA $574 total
includes taxes & fees
Jun 13 - Jun 14
Cheeca Lodge & Spa
Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1322)
"Guy making omelette was awesome"
The price is CA $272
CA $360 total
includes taxes & fees
May 19 - May 20
Chesapeake Beach Resort
Islander Resort
3 outdoor pools, cabanas (surcharge), pool umbrellas
Islander Resort
4.0 star property
9.0 out of 10, Wonderful, (1002)
"Absolutely beautifully appointed room and patio. Our family loves this resort. "
The price is CA $327
CA $443 total
includes taxes & fees
May 22 - May 23
Islander Resort
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Good"
The price is CA $209
CA $283 total
includes taxes & fees
May 16 - May 17
Drop Anchor
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers
Islander Bayside Villas and Boatslips
3.5 star property
9.0 out of 10, Wonderful, (335)
"Lovely sister property to the Islander - Resort; the, Islander Bayside resort Townhomes are wonderful. The Green Tuttle Inn. And the NEST across overseas highway great spirits & food. kitchens open until 10pm. 7 am green turtle breakfast. Or Mangrove Mike’s is a short walk North for breakfast. First night we walked to Lorelei, (15 minutes walk) for sunset. Best spot. This property is Slightly less than 2 miles NORTH from Bud and Mary’s marina and Lazy Days. Ideal for family or larger...
The price is CA $392
CA $516 total
includes taxes & fees
May 27 - May 28
Islander Bayside Villas and Boatslips
La Jolla Resort
View from property
La Jolla Resort
2.5 star property
8.8 out of 10, Excellent, (893)
"Nice room. Loved the dock and pool area. "
The price is CA $231
CA $260 total
includes taxes & fees
May 16 - May 17
La Jolla Resort
Sands of Islamorada
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio
Sands of Islamorada
2.5 star property
8.8 out of 10, Excellent, (324)
"Super Clean rooms, nice staff, TV was basic, easy on -off highway. Nice restaurants within walking distance. "
The price is CA $235
CA $264 total
includes taxes & fees
May 20 - May 21
Sands of Islamorada
La Siesta Resort & Villas
Aerial view
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1000)
"It was excellent, but could use a microwave in room"
The price is CA $400
CA $525 total
includes taxes & fees
May 19 - May 20
La Siesta Resort & Villas
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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.