Windley Key Holiday Rentals

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Holiday Rentals in Windley Key

Property grounds
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
10.0 out of 10, Exceptional, (2)
"We stayed for a week in late April. The location couldn't be better, and having a boat dock was amazing. We had lots of pool time and time on the water. The house had everything we needed to make our stay in Islamorada a dream. We'll be back for sure!"
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very good, (328)
"Love it!"
The price is HK$1,262
HK$1,824 total
includes taxes & fees
12 Jun - 13 Jun
Breezy Palms Resort
Beach/ocean view
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, (315)
"Absolutely beautiful! Cant wait to come back and stay here again."
Mangrove Marina and Resort Aqualodge Houseboats
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Property grounds
Amazing Ocean view at Ocean Pointe w/Heated Pool
9.6 out of 10, Exceptional, (9)
"The condo was nicely decorated. The kitchen was well stocked with everything for cooking. The beds were comfortable and plenty of bath and beach towels. Bring your own necessities, tp, paper towels, shampoo, soap everything else was there! The pool and beach are fantastic! We enjoyed our stay and would definitely stay again!"
Amazing Ocean view at Ocean Pointe w/Heated Pool
Private beach, sun-loungers, beach umbrellas, beach towels
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, (72)
"Amazing spot. Will definitely be coming back! "
Island Bay Resort
Property grounds
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (60)
"My family and I had a fantastic visit. The Home was very clean and the property was beautiful."
VOTED BEST KEY LARGO VACATION RENTAL
Property grounds
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, (116)
"Perfect place, everything you will need and more! The owner is great at communicating and is will to quickly resolve anything that needs resolved!"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Beach
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (24)
"House was just as described. It was in the perfect location with supermarket and restaurants nearby. The house was super clean and had everything we needed for a relaxing vacation. My husband and son enjoyed fishing from the jetty and my daughter enjoyed sunning by the pool. We also enjoyed snorkeling in the lagoon and the beach. We're so happy we found this treasure. Can't wait to visit again!"
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Property grounds
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
10.0 out of 10, Exceptional, (138)
"Very nice."
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Outdoor pool, a heated pool
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
9.8 out of 10, Exceptional, (179)
"Our stay was amazing from start to finish. The condo was beautiful and complete with everything we needed. The pool was perfect and allowed for night swimming after long days of recommended activities. The whole experience was great and I was telling everyone back in WI that it needs to be added to their accommodation list. Quiet and close enough to some really great restaurants as well. Felt like home!"
The price is HK$1,757
HK$3,700 total
includes taxes & fees
4 Jun - 5 Jun
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Beach
Beautiful Modern House in Key Largo
10.0 out of 10, Exceptional, (25)
"This property was amazing. The house is newly remodeled and done in a very modern way. The owner was very good with communication and I would highly recommend staying at this location."
The price is HK$1,757
HK$3,994 total
includes taxes & fees
2 Jun - 3 Jun
Beautiful Modern House in Key Largo
Fridge, microwave, oven, stovetop
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.6 out of 10, Exceptional, (31)
"After we got use to walking on our knees upstairs and I figured where the smoke alarm was (kept hitting my head), we loved the tiny house. It was clean and just as pictured! The house amenities were fabulous. We had everything we needed. The mattresses were so comfortable. The location was perfect for exploring the offerings at Key Largo and driving to all the other keys up to Key West. I would definitely do it all over again."
The price is HK$1,577
HK$3,621 total
includes taxes & fees
17 Jun - 18 Jun
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Beach
Lady Blue Yacht in FL KEYS
7.0 out of 10, Good, (4)
"We loved the experience until we couldn't access the WiFi for the television. There were a couple of wet places in the forward bedroom and bed, dirty underwear and shorts were left in the washer. We loved it though!"
The price is HK$1,718
HK$2,859 total
includes taxes & fees
30 May - 31 May
Lady Blue Yacht in FL KEYS
Property grounds
Beautiful Escape In Paradise
7.0 out of 10, Good, (2)
"It took us little longer to find out how things worked. Only thing is the toilet had no water the last day"
Beautiful Escape In Paradise
Outdoor dining
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
10.0 out of 10, Exceptional, (235)
"Clean and comfortable! We really enjoyed our stay."
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Outdoor dining
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
9.2 out of 10, Wonderful, (59)
"Dated RV that fulfilled our needs as an older couple. The host was wonderful! The grounds were very nice and the location made it easy for us to visit all the Keys. We had never lived in an RV before and the pull outs were nice. It had a few issues due to age, but we improvised and went with the flow. Enjoy your island time."
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
Property grounds
Key Largo Relaxing Getaway
9.8 out of 10, Exceptional, (75)
"The property has all we needed, ii was clean and quiet. It was the perfect place for a weekend getaway. Also, the communication with the host was very easy. I highly recommend it."
Key Largo Relaxing Getaway
Beach
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
10.0 out of 10, Exceptional, (162)
"This place was exactly what we needed to get everything ready for our son’s wedding. We loved the kitchen for all of the desserts we made. It was nice to be so close to the pool. There was so much space to spread out. It’s a wonderful place to stay."
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Beach/ocean view
Key Largo Cottages
2.5 star property
9.4 out of 10, Exceptional, (17)
"My daughter and I stayed here for a weekend. Had a fabulous time! Everyone was very nice and helpful. We went out in a canoe and used the snorkeling equipment. "
Key Largo Cottages
Outdoor dining
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
9.8 out of 10, Exceptional, (149)
"Great Place to stay. Spacious and very clean."
The price is HK$3,459
HK$6,851 total
includes taxes & fees
9 Jun - 10 Jun
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
Don't see what you're looking for?
See all available properties in Windley Key
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.

Other types of properties in Windley Key you may be interested in

Outdoor pool, pool loungers
Coconut Cove Resort and Marina
2.5 star property
7.4 out of 10, Good, (660)
"A nice quiet property. Plenty of parking. "
The price is HK$1,085
HK$1,221 total
includes taxes & fees
30 May - 31 May
Coconut Cove Resort and Marina
Exterior detail
Fisher Inn Resort & Marina
3.5 star property
7.6 out of 10, Good, (1000)
"I stayed here for one night after leaving Sugarloaf key, to be nearer friends and also the Miami airport. It was wonderfully appointed (room), clean and totally updated. Great view with a balcony too! "
The price is HK$1,118
HK$1,512 total
includes taxes & fees
11 Jun - 12 Jun
Fisher Inn Resort & Marina
Beach/ocean view
Drop Anchor
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Amazing place!"
The price is HK$1,022
HK$1,423 total
includes taxes & fees
30 May - 31 May
Drop Anchor
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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Recent reviews of Windley Key properties
Expedia verified reviews

Amara Cay Resort

Amara Cay Resort

5/5 Excellent
"They are under new management and have made some nice changes. Beach towels are now by the pool, metal water bottles are given at check in and water stations are available to refill them. Free shuttle service is offered within a range. We used it every night to take us to dinner. Lunch at the pool bar is very good."
A verified traveller stayed at Amara Cay Resort
Posted 1 day ago
Amara Cay Resort