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, (366)
"Property was recently remodeled and looked great. Have stayed here in the past so it’s right where I want to be. Close to world’s best fishing and great restaurants. Will be back soon."
The price is HK$861
HK$1,372 total
includes taxes & fees
10 Nov - 11 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, (324)
"The staff is amazing and all their recommendations were on point "
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, (16)
"This was our 12 wedding anniversary trip and we couldn’t have enjoyed it more! The property was so quiet (which we loved), the unit was beautiful and the view was breathtaking! Def recommend it! "
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, (86)
"This resort is great! Small run resort with great views. Small cottages that have a patio and a grill to use if you wanted to! The propert is beautiful and very clean! Kayaks and snorkel gear available to use when you want. I will def go back in the future "
Island Bay Resort
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, (42)
"If you have been wanting to try a tiny house, this is a fun one. Well equipped, mostly. It was clean and comfortable. The Kampground is quiet and safe. It is right in the middle of Key Largo. We would stay there again."
The price is HK$941
HK$2,821 total
includes taxes & fees
6 Nov - 7 Nov
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio
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
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, (38)
"Keys history Great location thoroughly enjoyed"
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
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, (150)
"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!
Lady Blue Yacht in FL KEYS
Beach
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 HK$2,022
HK$3,253 total
includes taxes & fees
6 Nov - 7 Nov
Lady Blue Yacht in FL KEYS
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$2,720
HK$5,225 total
includes taxes & fees
17 Nov - 18 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, (135)
"Property was clean and well kept and we had everything we needed for the stay. The resort also had plenty of things to do as well and Key Largo is beautiful. "
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
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. "
The price is HK$1,555
HK$3,395 total
includes taxes & fees
1 Dec - 2 Dec
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
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
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
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$706
HK$2,232 total
includes taxes & fees
6 Nov - 7 Nov
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
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
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, (246)
"Jorge was a most accommodating host! We had to switch a few days for unforeseen circumstances and he really worked with us. The unit itself was just as pictured, very clean and nicely appointed… probably has the BEST view in the whole place! Ocean Pointe was very nicely kept, always a ground crew around making sure. Very quiet… great place!"
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
On the beach, sun-loungers, beach towels
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
9.8 out of 10, Exceptional, (154)
"The condo was inviting and a home away from home. Nice to have straight access to pool area from back patio. The pool was good size. No hot tub. Most days pool was not crowded except for Saturday afternoon and evening there was a large crowd that met there and had very loud music with that could be heard throughout condo with doors closed. You are able to hear your neighbors and kids from the condo if they are loud which most kids are . Having golf cart to go to the jetty beach side is very nice...
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- BEACH- POOL-FISH
Key Largo Relaxing Getaway
Marina
Key Largo Relaxing Getaway
9.8 out of 10, Exceptional, (80)
"This was the perfect place for a quick anniversary getaway. The campground is very centrally located in Key Largo. The weather wasn’t great, so we didn’t get to use the pool or paddle board from the campground as we had planned. There was plenty to do in town though. "
Key Largo Relaxing Getaway
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

Drop Anchor
Beach/ocean view
Drop Anchor
3.0 star property
8.8 out of 10, Excellent, (1004)
"Is a beutifull place to relax ."
Drop Anchor
Fisher Inn Resort & Marina
Exterior
Fisher Inn Resort & Marina
3.5 star property
7.6 out of 10, Good, (1004)
"Great sta, can't wait to get back. Staff helped with fishing charter and restaurant recommendations. Private beach meant we could spread out and relax! "
The price is HK$1,043
HK$1,427 total
includes taxes & fees
6 Nov - 7 Nov
Fisher Inn Resort & Marina
Coconut Cove Resort and Marina
Outdoor pool, pool loungers
Coconut Cove Resort and Marina
2.5 star property
7.4 out of 10, Good, (681)
"Great spot. Beautiful views. Great pool. Staff friendly "
The price is HK$1,003
HK$1,128 total
includes taxes & fees
18 Nov - 19 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.