Windley Key Vacation Rentals

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Vacation Rentals in Windley Key

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
10.0 out of 10, Exceptional, (4)
"Our family of 5 stayed here over Christmas and had a wonderful time. The house had everything we needed. We hope to return soon!"
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very Good, (355)
"Everything was great ! Thank you. "
The price is ¥13,426
¥17,415 total
includes taxes & fees
Sep 29 - Sep 30
Breezy Palms Resort
Amazing Ocean view at Ocean Pointe w/Heated Pool
9.6 out of 10, Exceptional, (13)
"The condo was very nicely furnished, the kitchen had everything we needed and more and the unobstructed ocean view is amazing. We were able to cook several meals in the kitchen with all of the conveniences of home. The TV's worked fine and the property managers were incredibly efficient with providing the check-in details and wifi information. The community pool was a bit crowded but we were still able to find seats. We visited the private beach and pier and there were plenty of lounge seats...
Amazing Ocean view at Ocean Pointe w/Heated Pool
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, (322)
"Loved the peaceful atmosphere that the houseboat offered. Had everything we needed. Staff was very friendly and helpful. Absolutely loved the two decks off the back of the boat. Location was excellent. Would definitely consider staying here again if we’re ever back in the Keys!"
Mangrove Marina and Resort Aqualodge Houseboats
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (66)
"Wonderful place to stay and relax. Beautiful water"
VOTED BEST KEY LARGO VACATION RENTAL
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, (85)
"Outstanding property! Staff extremely attentive and professional. Grounds are meticulously kept, calm, beautiful without the crowds and busyness. Well appointed room that is comfortable with the smallest touches that made the stay unique. Will definitely be back- no reason to stay anywhere else!"
Island Bay Resort
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (38)
"Fantastic place in a quiet yacht club with a lagoon just outside the back porch for swimming, snorkelling, and kayaking. Accommodation was great and worked very well for us (2 adults, 3 children). Would absolutely stay there again. Highly recommended!"
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
10.0 out of 10, Exceptional, (148)
"This property is in a great location. The condo was fully stocked with dishes ice maker Keurig Machine plus regular coffee machine. Plenty of towels and kids toys in closet. View is good the property views are great. To bad the cafe was closed that would have been great to get breakfast and dinner there. Just wish the sofa was more comfortable and the tv was able Stream airplay or stream Netflix . The A/C works well . Not split unit .will definitely stay again next time down . "
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Beautiful Modern House in Key Largo
10.0 out of 10, Exceptional, (32)
"The house is very clean and well equipped. The host was quick to respond and very polite. Awesome place for two couples for a get away to the keys with the creature comforts of home. "
The price is ¥35,553
¥77,612 total
includes taxes & fees
Oct 2 - Oct 3
Beautiful Modern House in Key Largo
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, (130)
"Host Ken was fantastic and has a great place that we would most certainly stay at again. Communication was prompt and helpful. Loved the Place and loved Key Largo. "
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
9.8 out of 10, Exceptional, (193)
"Property is easy to access and on-site staff are friendly and helpful. Unit is comfortable and owner has lots of suggestions for things to do! Highly recommend!!"
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Lady Blue Yacht in FL KEYS
7.2 out of 10, Good, (5)
"We were looking for a different type of experience. We found it! However, the boat had been moved to a different city and we were not informed until 2 days prior to our stay. The new location offered nearby bars, restaurants, and live music that made our experience nice. Staying on the water and people watching from the boat deck was nice. The actual boat was very old and outdated. It could use some TLC."
The price is ¥26,309
¥46,059 total
includes taxes & fees
Oct 1 - Oct 2
Lady Blue Yacht in FL KEYS
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.4 out of 10, Exceptional, (37)
"Drove from Cape Coral to have a relaxing birtgday weekend! It was perfect! Went on a snorkel excursion, hung out in the pool, brought bikes and went on bike ride. Just a short ride to the national park! Everyone was so nice! Met people as we walked in the park! Great stay! Just what I needed!"
The price is ¥18,584
¥53,278 total
includes taxes & fees
Oct 2 - Oct 3
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Beautiful Escape In Paradise
8.0 out of 10, Very Good, (3)
"Great location to get to everywhere we needed to in Key Largo!"
Beautiful Escape In Paradise
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
9.4 out of 10, Exceptional, (64)
"The place was clean; everything worked as it should. It was in close proximity to a bathhouse and laundry service also. Nice, quiet community. Would definitely stay here again. Host was super and great about communicating despite the fact that we had a glitch on our end from not receiving our messages! Jeff took it all in stride and made sure we were taken care of!!"
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
Key Largo Relaxing Getaway
9.8 out of 10, Exceptional, (79)
"Felt like home"
Key Largo Relaxing Getaway
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
10.0 out of 10, Exceptional, (245)
"Great day fishing "
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
9.0 out of 10, Wonderful, (22)
"People are really nice super easy going perfect for a little weekend get away"
The price is ¥11,365
¥38,793 total
includes taxes & fees
Oct 1 - Oct 2
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Villa Largo Island Retreat
9.6 out of 10, Exceptional, (28)
"Beautiful resort property. Our family had a fantastic time there. Love the lagoon!!!! Thank you so much for the precious memories!"
Villa Largo Island Retreat
The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (38)
"We came the Labor Day weekend, to celebration two birthdays. It was a first for our family and we were pleasantly amazed by the property and all its amenities. We kayaked, sailed, played pickleball, biked and had a lot of fun overall. Our elderly mother was able to very comfortably relax inside, while enjoying the breathtaking views of the ocean from our balcony. We travel internationally several times a year,and this was one of our most relaxed vacations! But most noteworthy is the staff...they...
The Islands of Islamorada
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Other types of properties in Windley Key you may be interested in

Drop Anchor
3.0 star property
8.8 out of 10, Excellent, (1003)
"."
The price is ¥16,880
¥23,967 total
includes taxes & fees
Oct 6 - Oct 7
Drop Anchor
Coconut Cove Resort and Marina
2.5 star property
7.4 out of 10, Good, (676)
"Amazing all the way around!"
The price is ¥18,345
¥20,639 total
includes taxes & fees
Oct 1 - Oct 2
Coconut Cove Resort and Marina
Fisher Inn Resort & Marina
3.5 star property
7.6 out of 10, Good, (1000)
"Hotel was good. We enjoyed our stay."
The price is ¥20,815
¥28,144 total
includes taxes & fees
Oct 14 - Oct 15
Fisher Inn Resort & Marina
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.