Holiday Homes in Windley Key

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Featured Holiday Homes in Windley Key

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (68)
"Such a neat complex. Very safe and quiet. The kayaks were nice for the lagoon. I loved all the fish and everyone was nice that was staying there. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (19)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (31)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Sea La Vie! Fall Deals & Spring Openings- 4BR Key Largo Retreat

10.0 out of 10, Exceptional, (138)
"You would be very hard presses to find a better Key Largo location. Especially for family, boating and fishing!"
The price is AU$1,421
includes taxes & fees
3 Sept - 4 Sept
Sea La Vie! Fall Deals & Spring Openings- 4BR Key Largo Retreat

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (58)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is AU$685
includes taxes & fees
3 Sept - 4 Sept
Charming Home in Key Largo

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (84)
"Enjoyed greatly!Fantastic host!!"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (57)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

10.0 out of 10, Exceptional, (9)
"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

Amazing Florida Keys Retreat!

10.0 out of 10, Exceptional, (70)
"Great location and quiet. Very clean and had all the amenities for a great relaxing stay. "
Amazing Florida Keys Retreat!

Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

10.0 out of 10, Exceptional, (44)
"Loved the time with family- great location "
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.6 out of 10, Exceptional, (74)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is AU$529
includes taxes & fees
3 Sept - 4 Sept
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

10.0 out of 10, Exceptional, (105)
"We loved everything about this house! The outdoor areas were perfect. We had everything we needed to have a great time at the house but close enough to venture out and explore the keys if we wanted. Owners were responsive and great to work with"
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

10.0 out of 10, Exceptional, (3)
"Great house and very responsive host."
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (203)
"This property was very clean and comfortable, and the property manager was super responsive when we had questions. I would definitely recommend this rental to family and friends!"
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 star property
10.0 out of 10, Exceptional, (19)
"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

8.0 out of 10, Very good, (6)
"Three generations stayed very comfortably in this great house. It was located great for food and activities!"
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (119)
"Very clean, good location, easy access to boat ramp/dock"
The price is AU$598
includes taxes & fees
7 Sept - 8 Sept
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Kawama L4 - Upscale Oceanside Villa with Marina

9.6 out of 10, Exceptional, (136)
"This property was perfect in the heart of key largo with pool and ocean access. Had everything we need and even included two bikes! Great stay overall!"
The price is AU$895
includes taxes & fees
21 Sept - 22 Sept
Kawama L4 - Upscale Oceanside Villa with Marina

Beautiful Oceanside Mariner's 3 Bedroom Townhome

10.0 out of 10, Exceptional, (82)
"Great communication, beautiful property and close to lots of great restaurants and attractions. "
The price is AU$850
includes taxes & fees
3 Sept - 4 Sept
Beautiful Oceanside Mariner's 3 Bedroom Townhome
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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Top Windley Key Hotel Reviews

Find out more about Windley Key

Find out more about Windley Key

Windley Key Holiday Homes information

Number of reviews
Accommodation
647 Holiday Homes
Lowest Price
AU$529
Highest Price
AU$1,421

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