
Waterfront vacation rentals in Windley Key
Find and book unique waterfront accommodations on Airbnb
Top-rated waterfront accommodations in Windley Key
Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Windley Key waterfront rentals
Waterfront apartment rentals

Beachside Unit 22 - Private Beach on Atlantic
Had a great stay here. Very nice and great location in the keys.

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
Norma’s place was great! Norma was super helpful with recommendations, quick communication, and her place was comfortable & perfect for the 4 of us (2 couples). Can’t wait to come back.

Key Largo, Florida - Gem by the Sea
We had a great time at Diana’s place. We loved being able to use the available kayaks and fishing gear! Diana was super responsive and gave us some great recommendations. Moon bay was the perfect choice for our family of 5! Thanks Diana

#1 Island Hideaway 89 - OCEAN FRONT
Rhonda's place is terrific! Lovely location with full water views. Pool was excellent. The home was very comfortable, clean and convenient to restaurants and stores. Would definitely rent again.

Escape to the Seaside!
Perfect spot for a long weekend beach getaway! This was our first time visiting the Florida Keys, and we loved being right on the water with a small beach area to ourselves. The space was ideal for our group of friends, and the location was great—close to local bars and restaurants, some within walking distance or just a short drive away.

Ocean Side Paradise Awaits!
Condo was exactly as pictured. Beautiful resort and everyone very friendly onsite. Great location and close to lots to do. Cannot wait to book again.

Boho FL Keys Condo
The location, condo, grounds, access to restaurants and proximity to our fishing destination made this stay enjoyable. At the top of our list for our next trip.

Beachfront Condo w/ Ocean Views in Marathon
This is a beautiful ocean-front condo!! It is equipped with everything needed to spend a week or many weeks. The view is incredible, the beach is very nice and walkable. It is quiet, relaxing and the pool is at least 85 in January!! Enjoyed our week very much and hope to come back for a few weeks next time!!
Waterfront house rentals

Dock, Beach Club, January avail., tennis, golf
We loved our stay at Jeffery's house. It is spacious and very comfortable. My husband appreciated the proximity to the pickleball courts - we could see them from our bedroom windows- and my son enjoyed fishing off the dock. The upper suite was wonderful for privacy and quiet when the older kids stayed up later than the adults. Jeffery was super helpful and responsive. We would love to stay here again!

Dock Pool Ramp Jacuzzi Ocean Views Kayaks
House was nice and clean. Great location perfect for getting to open water. Frank was very helpful and responded quickly with any questions we had. I would recommend this place and would stay here again.

Luxury Waterfront Retreat with Dockage & Pool
We enjoyed our stay. The home was comfortable and very clean. It was nice to have a view of the water and a heated pool! The rooms were comfortable and accommodating for our family. Naomi was quick to respond when we had questions. I would stay here again! This spot was close to many restaurants, grocery stores, and right on bike paths!

A Pirates Great Escape ~ 3bed/2baths Ocean View B
Enjoyed the open space this rental had to offer. Very clean. Great views. Quiet location. Beds were very comfortable. The binder with all of the rentals information and suggested restaurants and things to do was very helpful!

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
We didn't know anything about Key Colony so based our reservation strictly on reviews and price. Well worth every penny that was spent. What a wonderful tropical getaway! Can't wait to visit the Keys again with my 4 children and husband. If you're looking for a great place to spread out and enjoy family this should be your rental.

Paradise Palms~ Open Water Views w/ 40' Dock, Pool
This home and location are exceptional!!! Everything about it exceeded our expectations, and I wouldn’t hesitate to rent a vacation home from Coco Plum again. It is expensive, but when you look at all you get and the location, it’s actually a bargain. The owner really has an exceptional home! Our family had a great time, and we will be back next year. Thank you!

Easy Ocean Access 30' Dock House Pool Cabana Club
The hosts were so accommodating and friendly. The space was newly remodeled with excellent quality and style of workmanship. It was also immaculately clean and incredibly well stocked. Our family of five (three young adult boys) was always comfortable. The hosts thought of everything you could want on vacation. They worked with us to make sure we had a place to dock and use our wave runners, there was outdoor dining and grilling space, complete with a filtered ice machine and an outdoor chest fridge for any fishing, a beautiful spot overlooking the canal, a pergola over the sitting area to provide extra shade, and the house itself was gorgeous and well appointed with plenty of space. We’d love to visit again!

Sunsets In Palms Paradise
The house was great, and the backyard amazing! Dolphins right next door, lots of shore birds, and fishing right from the dock. Hot tub under the stars, kayaking in the morning. Really great place to spend part of our spring break
Waterfront condo rentals

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Reel Large END Unit in Ocean Point Suites
Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.

Kawama Breeze
The host included touches of home which made the condo an even better value for our stay. For example, a few dish washer pods and laundry pods were included so we could avoid buying our own. Everything was spotless clean upon our arrival, along with the place being exactly as pictured and described. Bonus that the complex play area was nearby for my young kids (not too close to be noisy though). We are already talking about coming back and trying to stay at this location again. The location is great being so close to many activities and restaurants while feeling secluded and comfortable. The host is very responsive and accommodating for all requests we had. We definitely highly recommend this host and this property!!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again

Ocean Views at Ocean Pointe
Michelle was great! Very responsive and understanding when we had to make a last minute trip change. Unit was clean, bright and had a nice view. It’s a nice location between Key Largo and Islamorada making it convenient to explore both. We didn’t use any of the resort’s amenities, but there was an influx of seaweed at the small beach. Just one downside of this time of years in the Keys. But the pool looked great!

Modern and Coastal Ocean Pointe 2307
Exactly as pictured! Beautiful getaway in the Keys! It was very clean, even up to my picky healthcare expectations! Had everything we needed! A few more towels would have been great but we made it work. Kitchen stocked with all we needed. It was great to know what amenities and products were included and how much up front. The recommendation book was awesome! Beds were comfortable, all tvs worked well. Nice to have cable included too! The pool was absolutely beautiful, especially at night. Very clean facility outdoors as well. The beach area was probably the only disappointment, and out of their control. Just wasn’t as sandy etc. as we thought from pictures. Still very nice. It was also so nice to have a door code and not worry about a key. The neighborhood was welcoming too and safe to go for a morning run. All in all we would highly recommend this condo for your Keys vacation, family or couple! Our family of 6 fit :). Thanks for a great home away from home!

Bright & Sunny Suite w/ Magnificent Ocean Views
Beautiful views, well appointed condo, great amenities and location is very convenient.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!
Destinations to explore
- Florida Keys Vacation rentals
- Miami Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Central Florida Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Kissimmee Vacation rentals
- Tampa Vacation rentals
- Beachfront rentals Windley Key
- Rentals with a washer and dryer Windley Key
- Fitness-friendly rentals Windley Key
- House rentals Windley Key
- Pet-friendly rentals Windley Key
- Family-friendly rentals Windley Key
- Rentals with outdoor seating Windley Key
- Rentals with a patio Windley Key
- Rentals with a kayak Windley Key
- Rentals with pools Windley Key
- Rentals with an EV charger Windley Key
- Rentals with beach access Windley Key
- Waterfront rentals Islamorada
- Waterfront rentals Monroe County
- Waterfront rentals Florida
- Waterfront rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Zoo Miami
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Biscayne National Park
- Cannon Beach
- Far Beach
- Monkey Jungle
- Windley Key Fossil Reef Geological State Park
- Deering Estate
- Theater of the Sea
- Sea Oats Beach
- Cocoa Plum Beach
- EAA Air Museum
- Sandspur Beach
- Long Key State Park
- Everglades Alligator Farm
- Keys' Meads
- Horseshoe Beach