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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

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

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Property grounds

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.6 out of 10, Excellent, (37)
"Word can not explain the place everything was the best and would stay again and again "
The price is ￥13,499
￥42,071 total
includes taxes & fees
Apr 30 - May 1
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Beautiful Modern House in Key Largo
Terrace/patio

Beautiful Modern House in Key Largo

10.0 out of 10, Exceptional, (42)
"Property was newly remodeled, very clean, and way to find."
The price is ￥42,822
￥85,787 total
includes taxes & fees
May 3 - May 4
Beautiful Modern House in Key Largo
Kampground Escape w/ Kayaks, Heated Pool & Marina!
Outdoor pool, a heated pool

Kampground Escape w/ Kayaks, Heated Pool & Marina!

10.0 out of 10, Exceptional, (10)
"Had a great time in a great place"
Kampground Escape w/ Kayaks, Heated Pool & Marina!
RELAX in your PRIVATE Oceanfront Cottage!
Exterior

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (106)
"Great location close to restaurants and everything else you may need!"
RELAX in your PRIVATE Oceanfront Cottage!
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Outdoor pool

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
Property grounds

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise
Great location -pool-boat ramp-marina-golf cart
Outdoor pool, a heated pool

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`
Property grounds

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
Interior

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!
Fridge, microwave, coffee/tea maker, toaster

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

10.0 out of 10, Exceptional, (2)
"We enjoyedour stay"
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
Kayaking, sailing, snorkeling Free w/ Cottage
Property grounds

Kayaking, sailing, snorkeling Free w/ Cottage

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

Cottage w/ FREE Sailboat, Kayak, Bikes & More

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

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
Property grounds

Bayside view Cottage , Free kayaks and sailboat

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

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

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

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
Property grounds

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, (177)
"Wonderful, well-maintained, clean home in paradise! Roger and Linda communicated before, during and after our stay to make sure everything was perfect. Morning coffee on the porch, lunch by the pool, and several delicious restaurants for dinner, nearby. Our teens had plenty to do from swimming, to fishing in the boat basin, and fishing charters out of Key Largo. A day trip to Key West is also very manageable. We loved the daily manatee visits to the boat docks on the property. A safe, quiet...
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, (459)
"We enjoyed our stay. It was a nice location, clean."
The price is ￥17,592
￥27,240 total
includes taxes & fees
May 6 - May 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, (58)
"Everything was perfect. Every detail has been thought of. The rooms were immaculate and so well decorated. The property is really well maintained. We loved all of the games around the resort as well. Highly recommend! "
The price is ￥76,002
￥93,371 total
includes taxes & fees
May 5 - May 6
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.