Windley Key Holiday Rentals

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Holiday Rentals in Windley Key

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
Beach
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
Exterior
Breezy Palms Resort
2.5 star property
8.6 out of 10, Excellent, (371)
"Beautiful views "
The price is HK$836
HK$1,344 total
includes taxes & fees
24 Nov - 25 Nov
Breezy Palms Resort
Mangrove Marina and Resort Aqualodge Houseboats
Beach/ocean view
Mangrove Marina and Resort Aqualodge Houseboats
3.0 star property
9.4 out of 10, Exceptional, (325)
"We normally stay in hotel rooms when we travel, so we thought it would be fun to try a house boat when I saw the option. We had all the comforts that a hotel provides, but with a way cooler atmosphere. Our only disappointment it that we didn't stay long enough to try the pool and restaurant. Good experience. We'd stay again."
Mangrove Marina and Resort Aqualodge Houseboats
Amazing Ocean view at Ocean Pointe w/Heated Pool
Terrace/patio
Amazing Ocean view at Ocean Pointe w/Heated Pool
9.8 out of 10, Exceptional, (18)
"Superb apartment. Amazing view. Nice bright kitchen / lounge. Well stocked. Lots of towels. Nice big pool and hot tub. Had a great time. "
Amazing Ocean view at Ocean Pointe w/Heated Pool
Island Bay Resort
Private beach, sun-loungers, beach umbrellas, beach towels
Island Bay Resort
2.5 star property
9.8 out of 10, Exceptional, (90)
"Great experience!! Inn keepers and staff were very warm and friendly. Grounds are maintained perfectly great stay!!"
Island Bay Resort
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio
VOTED BEST KEY LARGO VACATION RENTAL
10.0 out of 10, Exceptional, (67)
"5 of us really enjoyed our stay. Norman provided great information to enjoy using their bikes, face masks 7 snorkels, etc. Best part was snorkeling in the private "swimming hole" lagoon, with beach stocked with tropical fish.' We all want to return "
VOTED BEST KEY LARGO VACATION RENTAL
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
View from property
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
10.0 out of 10, Exceptional, (151)
"We were staying during Hurricane milton. We had questions and they were answered almost instantly. This property is clean and nice ammenities. I will definitely stay here next time im in the keys. Highlyreccommend"
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Fridge, microwave, oven, stovetop
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
9.4 out of 10, Exceptional, (43)
"This tiny home was AMAZING! We stayed here for a night on our way back from key west and it was the perfect place. The tiny home was super clean and had everything we needed. The beds were incredibly comfortable in both the loft upstairs and in the bedroom. Bathrooms were awesome as well. The campground was awesome and was very walkable, we didn’t use the pool or the beach access but both were close walking distance. Would definitely stay here again! There is a publix right outside of the...
The price is HK$1,076
HK$3,093 total
includes taxes & fees
10 Dec - 11 Dec
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Beach nearby
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
9.8 out of 10, Exceptional, (39)
"Property owner was exceptional to deal with and the property was very clean and cozy! The home had all the comforts of home. Enjoyed the pool, lagoon and my husband loved fishing off the jetty !! "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
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, (194)
" We had a great time in your wonderful condo! It was amazingly quiet outside and the views were awesome! My daughter loved the raccoons. "
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Beautiful Modern House in Key Largo
Marina
Beautiful Modern House in Key Largo
10.0 out of 10, Exceptional, (33)
"Very clean and very comfortable had every thing you would need to make your stay great and easy access to main highway. I would book it again if I ever go back to the Keys"
The price is HK$2,724
HK$5,232 total
includes taxes & fees
23 Nov - 24 Nov
Beautiful Modern House in Key Largo
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Beach nearby, sun-loungers, beach towels
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
9.6 out of 10, Exceptional, (138)
"Father and Son fishing trip - great locations, property described just as it was, and a great complex. Would highly recommend. "
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Beautiful Escape In Paradise
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
Lady Blue Yacht in FL KEYS
Beach
Lady Blue Yacht in FL KEYS
7.8 out of 10, Good, (6)
"We enjoyed our stay from beginning to end. The checking and check out was very smooth. Thank you so much!"
The price is HK$1,440
HK$2,521 total
includes taxes & fees
23 Nov - 24 Nov
Lady Blue Yacht in FL KEYS
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
Outdoor dining
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
Villa Largo Island Retreat
Beach
Villa Largo Island Retreat
9.6 out of 10, Exceptional, (29)
"This house was perfect for our families (4 adults and 3 toddlers). It was very relaxing, tons of space, and in a great location within walking distance to the shoreline. There was a playground, swimming pool, and a lagoon right outside our back door! Everything was beautiful and the host was very quick to respond to any questions we had. Definitely would recommend this property! "
Villa Largo Island Retreat
Key Largo Cottages
Beach/ocean view
Key Largo Cottages
2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
Key Largo Cottages
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Property grounds
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
9.0 out of 10, Wonderful, (23)
"Evacuating from Milton. Booking was easy and the place was a safe harbor."
The price is HK$689
HK$2,310 total
includes taxes & fees
11 Dec - 12 Dec
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Property grounds
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
10.0 out of 10, Exceptional, (247)
"The condo was perfect for our quick getaway. Clean, modern, comfortable and exactly as pictured. Breathtaking views from the balcony. The pool and other amenities were just lovely and well maintained. Jorge, the owner, was so accommodating and quick to respond to my questions. We would come back again for sure."
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
FALL'24 Sell-off Deals! Prime OCEANFRONT 1300sf LUX Condo-All Amenities of Home!
Property grounds
FALL'24 Sell-off Deals! Prime OCEANFRONT 1300sf LUX Condo-All Amenities of Home!
9.6 out of 10, Exceptional, (269)
"Condo was in perfect location with respect to getting to various areas of Key Largo and you can’t beat the short walk to the jetty to see beautiful sunsets. Condo had everything we needed for our stay there. This is our 2nd time staying at this particular unit and we’ll be back! "
FALL'24 Sell-off Deals! Prime OCEANFRONT 1300sf LUX Condo-All Amenities of Home!
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 types of properties in Windley Key you may be interested in

Fisher Inn Resort & Marina
Exterior
Fisher Inn Resort & Marina
3.5 star property
7.6 out of 10, Good, (1002)
"Good, clean"
The price is HK$1,084
HK$1,474 total
includes taxes & fees
3 Dec - 4 Dec
Fisher Inn Resort & Marina
Drop Anchor
Beach/ocean view
Drop Anchor
3.0 star property
8.8 out of 10, Excellent, (1000)
"Nice cute quiet place. "
Drop Anchor
Coconut Cove Resort and Marina
Outdoor pool, pool loungers
Coconut Cove Resort and Marina
2.5 star property
7.4 out of 10, Good, (682)
"Great spot. Beautiful views. Great pool. Staff friendly "
The price is HK$1,782
HK$2,005 total
includes taxes & fees
23 Nov - 24 Nov
Coconut Cove Resort and 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.
Beautiful view of the beach with palm trees

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