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, (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
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (379)
"Beautiful "
The price is HK$940
HK$1,460 total
includes taxes & fees
6 Jan - 7 Jan 2025
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, (326)
"Gorgeous view, generally quiet. Location just a short drive from numerous dining locations. Would 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

9.6 out of 10, Exceptional, (23)
"Went on a quick trip to the keys with my daughter and son in law. We loved the cleanliness of the condo. I already miss the water view. It had comfortable beds and everything you need. The pool area was great, with lots of chairs. The buildings could use some address info as they all look alike. Plenty of parking too. "
Amazing Ocean view at Ocean Pointe w/Heated Pool
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (69)
"The townhome was large and I liked the layout so everyone had their own space. There are multiple balconies which was one of our favorite places to hang out while there. The sunrise/sunsets at the beach were beautiful! We were busy so didn’t spend much time in the lagoon or pools but the grounds were well-kept. "
VOTED BEST KEY LARGO VACATION RENTAL
Island Bay Resort
Private beach, sun-loungers, beach umbrellas, beach towels

Island Bay Resort

2.5 star property
9.8 out of 10, Exceptional, (95)
"Terrific small property with all the amenities. Hosts, Sue and Steve were great."
Island Bay Resort
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, (153)
"Our stay was fantastic thanks to the hosts' recommendations and accommodations. "
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Beach nearby

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

10.0 out of 10, Exceptional, (41)
"The townhouse was great for our family and in a perfect location to explore the upper keys. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
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$2,333
HK$4,681 total
includes taxes & fees
23 Dec - 24 Dec
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, (140)
"Kwama was a nice place to spend a long weekend. The property facilities are a bit outdated and not as clean as we would have liked but the location was good and we enjoyed our time there visiting the sites. Pools and beach area are nice and the grounds were well maintained. Could use some nicer chaises in the pool area. Good place to stay for families. Area was safe to walk or ride bikes and the fish lagoon was very cool. Lots of pretty fish and very peaceful. "
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, (197)
"Everything is close on property and within walking distance. Super helpful staff."
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
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$2,177
HK$3,412 total
includes taxes & fees
6 Jan - 7 Jan 2025
Lady Blue Yacht in FL KEYS
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (45)
"my son stepped on nails that are under the carpet on 2nd level. none are exposed. FYI kitchen faucet pin hole leak "
The price is HK$1,428
HK$3,495 total
includes taxes & fees
7 Jan - 8 Jan 2025
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
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
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Marina

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.8 out of 10, Excellent, (25)
"The RV park is top notch. Many activities to keep kids busy and has laundry facilities, trash pickup - very well cared for. The RV we stayed in was roomy and fairly comfortable. It needs a little TLC and a bit more attention to detail in cleanliness. All in all, it waswonderful stay."
The price is HK$1,033
HK$2,695 total
includes taxes & fees
8 Jan - 9 Jan 2025
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo, Calusa, 2 bedroom 1 bath with screened in patio
Outdoor dining

Key Largo, Calusa, 2 bedroom 1 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 bath with screened in patio
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, (251)
"Gated community, pool, private beach access, beautiful home, could not have asked for more. View from the balcony was amazing, and could not get enough of it. This was our first time in the Keys, and we will look forward to coming back here. "
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

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 HK$3,456
HK$4,317 total
includes taxes & fees
12 Jan - 13 Jan 2025
The Islands of Islamorada
Florida Keys Getaway - Slps 4 - Ocean View
Property grounds

Florida Keys Getaway - Slps 4 - Ocean View

9.2 out of 10, Wonderful, (12)
"Very clean and cozy! Elevator is available for the upper floors. Quick walk to the beautiful clean heated pool and hot tub. Umbrellas are available at tables at the pool and plenty of sun chairs. Boat launch and dock slips available on the ocean side. Perfect location to be an hour from Miami or two hours from key west!"
The price is HK$1,361
HK$3,265 total
includes taxes & fees
23 Dec - 24 Dec
Florida Keys Getaway - Slps 4 - Ocean View
Key Largo Relaxing Getaway
Marina

Key Largo Relaxing Getaway

9.8 out of 10, Exceptional, (82)
"We enjoyed our 3 days at this property immensely. The grounds are wonderful and a great place to have kids. The kitchen is well equipped, lots of towels and linens. Our only negative impression was the bathroom is rather small and had a pretty significant lean to the floor. "
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, (1001)
"Amazing place! Beautiful area with great amenities. Only thing was really stiff beds. But if you like very firm mattresses…it’s a 5 star. That aside …we will definitely be back!! "
The price is HK$993
HK$1,389 total
includes taxes & fees
23 Dec - 24 Dec
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, (684)
"I like it"
The price is HK$1,159
HK$1,303 total
includes taxes & fees
23 Dec - 24 Dec
Coconut Cove Resort and Marina
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
7.6 out of 10, Good, (1004)
"Great location in the Middle Keys and close to all of the cool hang-outs! Also very clean, has a nice pool and my room had the best balcony view ever!!!"
The price is HK$1,580
HK$2,031 total
includes taxes & fees
8 Jan - 9 Jan 2025
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.