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Featured Villas in Windley Key

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Lovely room with friendly staff. "
The price is AU$1,508
includes taxes & fees
24 Feb - 25 Feb
The Islands of Islamorada

Newly upgraded Key Largo Villa W/Boat Slip

10.0 out of 10, Exceptional, (77)
"Great location and beautifully decorated home. Perfect boat parking and set up for a fishing family. Annie was super responsive and a great host. We can’t wait to book again!"
Newly upgraded Key Largo Villa W/Boat Slip

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

9.4 out of 10, Exceptional, (56)
"Location was close to many great restaurants. We could use the pool or go to the ocean. We will definately be back."
The price is AU$1,147
includes taxes & fees
22 Feb - 23 Feb
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Coral Breeze with Resort Privileges

10.0 out of 10, Exceptional, (1)
"I've stayed at a few of these houses but this was the first time staying at this one. Love the property. Awesome that they allow pets. Communication with the property manager was great. They were very helpful. Love the resort privileges. The upstairs outdoor patio was really comfy with a great view. I'll definitely stay again"
Coral Breeze with Resort Privileges

SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!

9.4 out of 10, Exceptional, (26)
"We visited with 9 adults and had a great week at the condo and pools. Having 2 stories worked out perfect for us. Our kids and their friends had a separate area to hang out. The place was clean and exactly as described, and the hosts provided clear instructions for arrival and departure. We had no issues all week and loved using the pools, hot tubs, exercise facility, and games room. Shopping was convenient, and we took a trip snorkeling as well. Everything you’d want was near-by."
The price is AU$1,768
includes taxes & fees
22 Mar - 23 Mar
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!

Sea-Esta with Resort Privileges

10.0 out of 10, Exceptional, (4)
"Beautiful! Beautiful! Beautiful! Location is perfect. House is incredible. Master bedroom and bath are just dreamy. Resort is super close and top notch. So much to explore inside and out. Could have lived there for a month. Kitchen needs a few things, pot upgrades for chefy folks, but nothing you can’t make do in a pinch. Salt and pepper are the only spices, for those who cook. You will not care when you’re floating out on the kayak, laying in the winter sun on the 3rd floor balcony, snuggled...
Sea-Esta with Resort Privileges

Gull's Nest with Resort Privileges

9.6 out of 10, Exceptional, (18)
"great layout. clean user friendly could use more forks spoons"
Gull's Nest with Resort Privileges

Sandcastle Luxury Villa in Key Largo with Resort Privileges

10.0 out of 10, Exceptional, (1)
Sandcastle Luxury Villa in Key Largo with Resort Privileges

MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!

9.6 out of 10, Exceptional, (40)
"Took a group of guys to go down for relaxation and fishing. Resort was perfect for relaxing. Condo itself was excellent and the heated pool and grotto were well used. If you choose to fish there is ample opportunity with local charters and the one day it rained we visited several local breweries. Perfect getaway."
The price is AU$1,515
includes taxes & fees
28 Feb - 1 Mar
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!

Isla Key Acaí: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Isla Key Acaí: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

10.0 out of 10, Exceptional, (89)
"This is a great spot to get to so many fun things to do in the keys. Whether you are driving, walking, or going by boat. It's a wonderful community with friendly people staying around you and a perfect spot for sunsets!"
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

9.4 out of 10, Exceptional, (60)
"This resort was the perfect blend of everything we needed for our stay. The condo was on a quiet street within walking distance to the hidden beach area, the tennis court, and the large oasis pool. And the clubhouse and separate pool and marina weren't far either. The layout of bedrooms on the 3rd floor, and base floor was great separation with the main living/cooking in the middle. The mini kitchen at the bottom was convenient as well. The place was nicely decorated, and updated (maybe an...
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

9.8 out of 10, Exceptional, (45)
"This property is amazing. In addition to being spacious the property my was clean, had a great location, and everything you need for a great Key Largo vacation. Definitely will be back."
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

Endless Summer with Resort Privileges

9.2 out of 10, Wonderful, (10)
"Great location. Everyone was very attentive. They went beyond during our stay and after. Resort is such a bonus. I've been a serval times and i highly recommend the property"
Endless Summer with Resort Privileges

Tranquility with Resort Privileges

9.8 out of 10, Exceptional, (6)
"Our flights were cancelled in Miami during our layover, and I was able to get into this condo the next day. The house was beautiful, and had everything we needed. Our family of five was able to spread out and get the space we needed. This property is roughly 1/2 mile from the playa largo resort where you get a welcome drink and are able to use the pool and all the activities of the resort are included with wristbands. There is also a pool for thre “residences” about 300 yards away from the...
Tranquility with Resort Privileges

Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

Tastefully Remodeled Island Villa in Key Largo, 2 Bedrooms, 2 Bathrooms.

9.6 out of 10, Exceptional, (152)
"The condo was bright, quiet and walkable to restaurants with good food and live entertainment. Furnishings and art work were very tasteful. Appliances were modern and updated and The washer/dryer made laundry convenient. The neighborhood was beautiful and safe. We had everything we needed for our month long stay."
Tastefully Remodeled Island Villa in Key Largo, 2 Bedrooms, 2 Bathrooms.

Latitudes with Resort Privileges

8.0 out of 10, Very good, (2)
"The house was nice, reasonably located. Our checkin was seamless and required only an email. The house was nice, clean, brand new and had reasonable furnishings. The house itself lacked many standard and or listed items such as a grill, adequate table ware, bedding, functional ice-maker, toaster, coat hangers, hair dryer, iron/ironing board… and trying to get the property manager to respond took 48 hours+. The walk to the resort is .6 miles but requires navigation across a four lane highway...
Latitudes with Resort Privileges

Sea Haven with Resort Privileges

10.0 out of 10, Exceptional, (1)
Sea Haven with Resort Privileges

Twilight with Resort Privileges

Twilight with Resort Privileges
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

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

10.0 out of 10, Exceptional, (172)
"The house we stayed in was immaculate and so attractive-exactly as pictured. We felt very safe in the gated community. We used the kayaks and pool and walked the area frequently. We rented bikes and had great areas to ride in. This was a very quiet, relaxing vacation. Lots of waterside restaurants to enjoy. The owner, Roger, was a great communicator."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (411)
"We only spent 3 nights, but our room was very clean and comfortable. We did have an oceanfront room, so the views were great! The room had a full kitchen and living room. I only wish there was a TV in the bedroom as well. We did not use the pool, but it looked very refreshing and well kept. The beach area was beautiful with plenty of seating, and the jetty for fishing was great for my husband. It was within walking distance to Lazy Days Restaurant and Bud & Mary's Marina. We stayed at several...
The price is AU$397
includes taxes & fees
13 Mar - 14 Mar
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Lovely room with friendly staff. "
The price is AU$1,508
includes taxes & fees
24 Feb - 25 Feb
The Islands of Islamorada
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.