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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

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

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Marina

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
Marina

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!
Marina

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!
Lake

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!
Miscellaneous

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
Outdoor pool, a heated pool

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
Outdoor pool

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise
Great location -pool-boat ramp-marina-golf cart
Shower, hair dryer, towels, soap

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`
Marina

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
Outdoor dining

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!
Marina

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
Marina

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage
Cottage w/ FREE Sailboat, Kayak, Bikes & More
Marina

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Marina

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
Marina

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Marina

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Free sailing, kayaking, water toys etc w/ Cottage
Marina

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.
Pool

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!
Interior

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
Marina

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
A heated pool

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
Exterior

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
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

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.