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Compare 21 Cottages in Windley Key with updated reviews, rates, and availability.

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

9.0 out of 10, Wonderful, (28)
"Nice facilities. Wish we had better weather. Always enjoy our home away from home. KEYS LIFE FOR ME!!!!"
The price is ¥26,277
¥60,479 total
includes taxes & fees
Feb 24 - Feb 25
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beautiful Modern House in Key Largo

10.0 out of 10, Exceptional, (36)
"Very nice and clean"
The price is ¥44,781
¥90,308 total
includes taxes & fees
Feb 24 - Feb 25
Beautiful Modern House in Key Largo

Kampground Escape w/ Kayaks, Heated Pool & Marina!

10.0 out of 10, Exceptional, (7)
"Really liked the campground. Heated pool, laundry and while fairly full also quiet. Lot 49 had wonderful outside seating and a nice spot for morning coffee. Very clean and loved the welcome amenities "
Kampground Escape w/ Kayaks, Heated Pool & Marina!

Luxury cottage in the heart of paradise

9.6 out of 10, Exceptional, (26)
"Enjoyed our stay. Location is perfect although there is no beach access just the marina. Close to everything and the place is very nice and clean"
Luxury cottage in the heart of paradise

Great location -pool-boat ramp-marina-golf cart

10.0 out of 10, Exceptional, (2)
"Good!"
Great location -pool-boat ramp-marina-golf cart

BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

Key Largo Cozy Cottage! Paradise Awaits you! Private Beach& Boat Ramp

10.0 out of 10, Exceptional, (2)
"My friend and I had a wonderful month at Sergio’s house. The place is very well kept and very clean. The outdoor furniture is where we sat the most. Near the beach and very nice sunset,including quiet neighborhood."
Key Largo Cozy Cottage! Paradise Awaits you! Private Beach& Boat Ramp

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise

Key Largo Home w/ Dock & Private Beach Access

3.0 star property
Key Largo Home w/ Dock & Private Beach Access

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Kayaking, sailing, snorkeling Free w/ Cottage

The price is ¥50,752
¥57,021 total
includes taxes & fees
Feb 23 - Feb 24
Kayaking, sailing, snorkeling Free w/ Cottage

1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

3.0 star property
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

Key Largo Paradise w/ Heated Pool & Hot Tub!

3.0 star property
Key Largo Paradise w/ Heated Pool & Hot Tub!

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

The price is ¥50,752
¥57,768 total
includes taxes & fees
Feb 23 - Feb 24
Cottage w/ Private Yard, Free Kayaks, Boats, Etc
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 property types in Windley Key

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

10.0 out of 10, Exceptional, (172)
"The house we stayed in was immaculate and so attractive-exactly as pictured. We felt very safe in the gated community. We used the kayaks and pool and walked the area frequently. We rented bikes and had great areas to ride in. This was a very quiet, relaxing vacation. Lots of waterside restaurants to enjoy. The owner, Roger, was a great communicator."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (413)
"Wonderful experience - highly recommend!! From check in to check out was great. All staff were very helpful, property was well kept, relaxing, quiet & very easy location to site’s & restaurants. "
The price is ¥26,512
¥37,577 total
includes taxes & fees
Mar 25 - Mar 26
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is ¥120,759
¥144,082 total
includes taxes & fees
Feb 24 - Feb 25
The Islands of Islamorada
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.