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Compare 24 Cottages in Windley Key with updated reviews, rates, and availability.

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.6 out of 10, Excellent, (32)
"Property was clean. There were some small ants in the kitchen and bath."
The price is ¥14,726
¥44,006 total
includes taxes & fees
Apr 30 - May 1
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beautiful Modern House in Key Largo

10.0 out of 10, Exceptional, (40)
"Great place."
The price is ¥44,952
¥91,253 total
includes taxes & fees
Apr 1 - Apr 2
Beautiful Modern House in Key Largo

Kampground Escape w/ Kayaks, Heated Pool & Marina!

10.0 out of 10, Exceptional, (8)
"Everything was absolutely perfect! We highly recommend this property!!"
Kampground Escape w/ Kayaks, Heated Pool & Marina!

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (103)
"Wonderful location, amazing ocean views, and clean/cozy cottage. Definitely will return. It was perfect for us! Thank you for sharing your home! "
RELAX in your PRIVATE Oceanfront Cottage!

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!

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

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece 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

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

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

10.0 out of 10, Exceptional, (4)
"Paradise was the perfect name for this property! It had such a lovely outdoor space and the owners were absolutely amazing! Everthing I needed was at the property. I highly recommend this home and would definitely stay again in the future."
Key Largo Cozy Cottage! Paradise Awaits you! Private Beach& Boat Ramp

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

10.0 out of 10, Exceptional, (1)
"We had an awesome time! The house was perfect for us and the host is fantastic! Loved the community and amenities! We would definitely stay again "
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

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

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

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage

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

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

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

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

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cottage w/ Full Kitchen FREE sailboats and kayaks
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, (175)
"Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (431)
"I loved the vintage Florida feel 0f the property."
The price is ¥30,139
¥41,674 total
includes taxes & fees
Apr 6 - Apr 7
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (54)
"Above and beyond service. "
The price is ¥86,757
¥105,861 total
includes taxes & fees
Apr 6 - Apr 7
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.