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Featured Villas in Windley Key

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (39)
"We loved the entire experiences; especially the amenities on site (kayaks, paddle boards, swimming-pool & ocean, food & bar) and Emmanuel (person responsible kayaks and paddle boards)."
The price is AU$920
includes taxes & fees
26 Jan - 27 Jan
The Islands of Islamorada

Sensational Ocean Front Villa Kayak+PBs+Cinema+Fire Pit+Pool License # 24-4115

9.8 out of 10, Exceptional, (65)
"Loved the property and had a great time but the luxury in the listing was not there. The biggest issue being the pergola in the pictures was gone and replaced with a single umbrella. The string lights in the backyard were broken and the majority of items were powered by extension cords laying on the ground, many with tripped breakers. The pool/hot tub was unable to be controlled and we needed to text someone whenever we wanted a change. The outdoor cinema experience was a projector in a box that...
Sensational Ocean Front Villa Kayak+PBs+Cinema+Fire Pit+Pool License # 24-4115

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

9.6 out of 10, Exceptional, (39)
"We really enjoyed our stay - very clean, beautiful pools, tennis and pickle ball courts well maintained. Would stay again!"
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!

Newly upgraded Key Largo Villa W/Boat Slip

10.0 out of 10, Exceptional, (76)
"The owners were very kind and communicative. Although they offered a different unit, everything was wonderful. We would like to recommend this rental to every one. You will get amazing staying in Key Largo. "
Newly upgraded Key Largo Villa W/Boat Slip

Sandcastle Luxury Villa in Key Largo with Resort Privileges

Sandcastle Luxury Villa in Key Largo with Resort Privileges

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

9.6 out of 10, Exceptional, (58)
"Absolutely breathing views. the kids loved the pools!!! The villa was amazing!!! Very beautiful!"
The price is AU$1,485
includes taxes & fees
6 Jan - 7 Jan
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

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$1,621
includes taxes & fees
20 Jan - 21 Jan
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!

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

9.4 out of 10, Exceptional, (55)
"Very nice. Excellent access to pool. "
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Hideaway with Resort Privileges

9.4 out of 10, Exceptional, (15)
"Very nice place the pool right by the house was actually our favorite"
Hideaway with Resort Privileges

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

9.6 out of 10, Exceptional, (151)
"Very nice property. Excellent view. Wonderful hosts"
Tastefully Remodeled Island Villa in Key Largo, 2 Bedrooms, 2 Bathrooms.

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

Tranquility with Resort Privileges

9.6 out of 10, Exceptional, (5)
"The townhouse was beautiful, clean and well stocked. Very quiet as only 3 townhomes are ready for guests. Andrea, the property manager was wonderful! Would stay again when traveling to the Upper Keys."
Tranquility with Resort Privileges

Sea-Esta with Resort Privileges

10.0 out of 10, Exceptional, (3)
"We went on a family get away for 3 days, 4 adults and 3 kids, 2 girls (6years old ) and one baby( 20 months ). We had an incredible time and can’t wait to come back but for more days. The house is perfect, super clean, well decorated and extremely well equipped. We have stayed at many apartments, houses with Vrbo in the past but this one by far has been my favorite. The manager Jossie really cares, the answered my texts right away, the check in was a breeze. She even contacted me even earlier...
Sea-Esta with Resort Privileges

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

2bd/2ba Ocean Retreat in Kawama Yacht Club

10.0 out of 10, Exceptional, (35)
"Condo was perfect for my family. Had everything we needed and was clean/comfortable. The host was friendly and communicated well. Kawama is a great resort with so much to offer."
2bd/2ba Ocean Retreat in Kawama Yacht Club

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

Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

10.0 out of 10, Exceptional, (10)
"Thank you Lourdes and Jose for a lovely home exactly as pictured to enjoy our son’s wedding nearby! We were able to relax a little before and after all the events! Your home was beautifully decorated and in perfect working order. It was well stocked with 3 different coffee machines to use and full sized stackable washer dryer. We appreciated the great cold Air Conditioning having to prep for many wedding events. There was comfortable furniture and decorator decor to rest your eyes upon. It made...
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

Sea Haven with Resort Privileges

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

Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**

10.0 out of 10, Exceptional, (24)
"Our experience was so wonderful I almost don't want to review the property so we can keep it our little secret! The property is amazing. The listing is a little hard to figure out in terms of layout so I'll start there. The entrance has parking for at least 10 cars. The first villa is a 2 bed 1 bath and is the main house. Villas 2 and 3 are 1 bed 1 bath and are set up like a duplex. Villa 4 is a 1 bed 2 bath plus an outdoor shower as well. Every villa has it's own stove, fridge, living room,...
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
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

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

10.0 out of 10, Exceptional, (5)
"We had a wonderful visit. We come every Thanksgiving. Anglers is wonderful place to stay."
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (386)
"Amazing place to stay and right near everything. Very authentic."
The price is AU$253
includes taxes & fees
5 Jan - 6 Jan
Breezy Palms Resort

Mangrove Marina and Resort Aqualodge Houseboats

3.0 star property
9.4 out of 10, Exceptional, (326)
"Gorgeous view, generally quiet. Location just a short drive from numerous dining locations. Would stay again!"
Mangrove Marina and Resort Aqualodge Houseboats
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.