Windley Key Holiday Rentals

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Check prices for these dates

Tonight
22 Jan - 23 Jan
Tomorrow
23 Jan - 24 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

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, (398)
"This is a great little place to stay at a very good rate. It is walking distance to some amazing restaurants. The room had been updated, it was clean. Staff was friendly but I wouldn’t say they go out of their way. The beach is good for relaxing at but it’s pretty shallow a long way out so not much for swimming. The pool was nice but you lose the sun early due to placement. I’d stay here again."
The price is HK$1,276
HK$1,839 total
includes taxes & fees
28 Jan - 29 Jan
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)
"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

9.4 out of 10, Exceptional, (26)
"Great location & View. We really had a fun weekend and this the condo was close to everything we needed. The one opportunity that we experienced was the toilet in the quest bath was very small and seemed like a children's size. The condo was well stocked and very clean."
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, (71)
"Great location. wonderful amenities and Norman was very helpful in explaining and touring the entire property Lots of attractions on the Key and many very good restaurants.."
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, (97)
"The property was beautiful and excellently maintained. Staff was dedicated, friendly, and helpful. Only negative was a slight unusual odor in our unit. While compact, the unit managed to have what was needed for a comfortable stay. A comfortable reading chair would be a nice addition."
Island Bay Resort
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, (44)
"This property was immaculate, a great blend of an upscale hotel feel with a vacation rental. We loved all the amenities. Would highly recommend!"
The price is HK$3,567
HK$4,442 total
includes taxes & fees
12 Feb - 13 Feb
The Islands of Islamorada
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, (43)
"Great location second bedroom a little cramped with two beds. Pools are good. Quiet setting and lagoon is nice, "
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, (157)
"Rental was very clean and stocked beach towels. Had small problem with lock and owners responded very quickly to solve the problem. Unit is very close to pool. Very nice place to stay!"
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Beautiful Modern House in Key Largo
Marina

Beautiful Modern House in Key Largo

10.0 out of 10, Exceptional, (34)
"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$2,336
HK$4,664 total
includes taxes & fees
25 Jan - 26 Jan
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, (141)
"Best equipped condo ever, also nice firm mattresses. The only little glitch, was getting the keys out of the lock box. This could be replaced! We would love to stay here again!"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
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$1,556
HK$3,688 total
includes taxes & fees
5 Feb - 6 Feb
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
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, (200)
"The unit was clean, spacious, great views! Our 2nd day the AC was not working and the owner got someone in there to fix it RIGHT AWAY! We loved our stay and had many great experiences in the area. My parents and brothers family each also had ocean point units and this one had the best kitchen, best views and was the most roomy."
The price is HK$2,334
HK$4,390 total
includes taxes & fees
9 Feb - 10 Feb
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!"
Lady Blue Yacht in FL KEYS
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 Resort, 2 bedroom 1 bath with screened in patio
Outdoor dining

Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio

9.4 out of 10, Exceptional, (66)
"Rented from the same host and was happy to see and hear that he upgraded his trailer. It is much nicer than the older one which was fine! It has a nice outdoor kitchen to enjoy as well! Very nice and enjoyable stay!!!"
Key Largo, Calusa Resort, 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, (254)
"This property was great, very clean and exceeded our expectations. The beach was pretty and pool was the perfect temp. The local kitties were a bonus. We loved seeing them throughout the day. This place was quiet and very well kept, We will be back. "
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
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$950
HK$2,610 total
includes taxes & fees
27 Jan - 28 Jan
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Florida Keys Getaway - Slps 4 - Ocean View
Property grounds

Florida Keys Getaway - Slps 4 - Ocean View

9.4 out of 10, Exceptional, (13)
"We loved the property amenities and the condo. Minor "
The price is HK$1,447
HK$3,371 total
includes taxes & fees
26 Jan - 27 Jan
Florida Keys Getaway - Slps 4 - Ocean View
LAST WK OF JAN STILL OPEN! RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
On the beach, sun-loungers, beach towels

LAST WK OF JAN STILL OPEN! RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!

9.6 out of 10, Exceptional, (172)
"When I go to all the trouble of actually writing a review, I’m going to be totally honest (& maybe a little picky.)We absolutely positively LOVED the view.The weather was cool (by FL standards) the week we stayed, and there was no hot tub although I saw “hot tub”somewhere on the listing. But the pool was heated. Nice 2 person kayak was available with life vests. I really enjoyed chilling & reading on the balcony & looking at the ocean & birds. The condominium has a modern recently renovated...
LAST WK OF JAN STILL OPEN! RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
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)
"Good value for the money. Enjoyed using the kayaks and paddle boards. Friendly staff. Very good location on the water."
The price is HK$1,486
HK$1,944 total
includes taxes & fees
23 Jan - 24 Jan
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, (699)
"The property itself is amazing. The room was very clean and comfortable. The staff and property manager are incredible - super friendly, helpful and accommodating. We’d definitely stay again!"
The price is HK$1,471
HK$1,654 total
includes taxes & fees
23 Jan - 24 Jan
Coconut Cove Resort and Marina
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1001)
"We had such a great experience! Nice room with a great view, friendly staff, dog friendly. The bikes, kayaks and paddle boards were a nice touch too!"
The price is HK$1,627
HK$2,085 total
includes taxes & fees
26 Jan - 27 Jan
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.