
Holiday rentals with outdoor seating in Windley Key
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Top-rated rentals with outdoor seating in Windley Key
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Windley Key
House rentals with outdoor seating

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024
We loved the house! Everything was exactly as described. I would even say pictures didnt do complete justoce to the space and views! We had everything we needed at the house with ample dishes and cookware. We drove down to Key West which wasnt too far of a trip. We definitely would always recommend and stay again! Jessieca was an amazing host with great recommendations and general info for the area.

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

Waterfront Home 37.5-ft dock, Cabana Club Included
Clean house, well decorated, great location and responsive hosts! It’s also a plus that they accept pets for a reasonable pet fee. Key Colony Beach is a great location and this is a lovely little home. Book with confidence!

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Mariners Club Resort, Best in the Upper Keys
The home is beautiful, well maintained, clean and perfectly set up for a large group. The house had literally everything we wanted plus additional thoughtful things that made our experience great! And.. All the amenities were just short a walk away. The host Joseph was very responsive and accommodating. Our family loved it here and will definitely return.

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach
Excellent place fun for the kids, the pool was amazing,the house has everything you need, the gulf cart was a plus. Highly recommended!

Bohemian Beach Bungalow
I can’t say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibe—exactly what you want for a beach getaway. Whether you’re looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and we’re already dreaming of coming back!

Captain’s Quarters Ahoy Mateys! Florida, Keys
The place was great. Very clean and was better than the pics. Back patio was amazing and we caught fish off the dock with the supplied fishing poles (after getting our fishing license of course). It was the perfect homebase as we explored the keys.
Apartment rentals with outdoor seating

*NEW* Sea La Vie - Pool & Beach
We just spent 6 days at Yuni's airbnb. Our family of four(all adults) could not have been happier with the peace and quiet this place offered us. The private beach and pool had plenty of chairs and umbrellas. We loved the balcony overlooking the pool and beach. We enjoyed how close it was to Havanna Jack's for a quick bite to eat and drink. Yuni's place was exceptionally clean. Plenty of bath towels and beach towels. The kitchen was fully stocked with all of our needs. She quickly responded to our questions and our needs. Yuni is one of the best hosts we have had throughout the years of using airbnbs. We definitely will go back!

Beachside Unit 22 - Private Beach on Atlantic
Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths
We absolutely loved our stay here!!! Norma worked to accommodate us even with our tight schedules and helped make our stay unforgettable! The rooms were spectacular, the lagoon was amazing and the view from the point was breathtaking! We will definitely make this our go-to place in Key Largo!

Turtles Nest 2 Ocean Point condo
Amazing condo! The view from the balcony is beautiful for sunrises and sunsets! My family had a great time at the pool and restaurant on the property. We will definitely be coming back! 😊

The HMH House
I had a lovely stay with my college daughter in the Keys. The place was just what we wanted. The decor was so beautiful and the grounds/pool area were so pretty. We were so sad to leave. Will definitely return. Heather Marie was amazing and such a wonderfully generous human. I can’t recommend this property enough.

Waterfront Studio 2| Couples Oasis | Kayaks | Pool
Our stay at this dockside Airbnb was absolutely perfect for the two of us. The home was spotlessly clean and had every amenity we could have possibly needed. Everything was exactly as described—if not better—and the attention to detail made it clear that the guest experience was a top priority here. The location, tucked into a peaceful boating community, made for a truly relaxing atmosphere. We loved being right on the water, and while we didn’t have time to use the kayaks they offered, it was such a thoughtful touch to have them available. Communication with the host was flawless. They were incredibly responsive, friendly, and accommodating throughout the entire process. It really made the whole experience feel seamless and welcoming. We would absolutely stay here again without hesitation. Highly recommend this place for anyone looking for a clean, comfortable, and guest-focused getaway on the water!

Boho FL Keys Condo
We really enjoyed our stay. The location is great and the view is amazing. It is very clean and very well maintained. Would definitely stay again.

Studio apartment in Calusa Resort & Campgrounds
So must say 10/10 we stay in a lot of places and this one we will deff come back to over and over again it was perfect and I must say the price is a steal honestly when we first booked we were nervous because of the price was cheap and I must say dosent reflect at all it is a amazing studio super clean super comfy can’t wait to come back highly recommend
Apartment rentals with outdoor seating

Newly Renovated Piece ofParadise
We had such a wonderful stay at Todd’s Airbnb in beautiful Key Largo! The place was modern, spotless, and thoughtfully decorated—it felt like a true home away from home. The kitchen was well stocked with everything we needed, which made cooking a breeze. There were so many fun things to do on the property, from grilling out on the BBQs to relaxing in the hammocks, and playing foosball or ping pong. The pool was awesome, and the marina was absolutely stunning—especially at sunset. Todd was an incredible host, full of helpful information and spot-on recommendations that made our trip even better. We’d highly recommend his place to anyone looking for a fun, comfortable, and well-located home base in Key Largo. Can’t wait to come back!

Waterfront Spacious Condo Key Largo #4, 10% Off 7+
Great stay at Javiers’s place. Beautiful views and great quiet neighborhood location. Bar and Restaurant a 2 minute walk away and everything else you could need a 5 minute drive.

Enjoy sunsets & sunrise in your home away home.
Great condo in a perfect location to access the best of Key Largo. The condo is in a nice complex, with a great pool, mini beach, and dock area. The unit was well stocked with beach & bath towels, all kitchen appliances, washer dryer with detergent & dryer sheets, spare cooler, charcoal & lighter fluid for the grill. The bedrooms were super comfy. I highly recommend staying here!

Million dollar view in Key Largo!
The condo was very nice. Lots of room, clean and easy to access. We loved the balcony, and spent a lot of time there. We enjoyed the kayaks a couple of different times as well. Our first time to The Keys and we enjoyed this spot.

Ocean views at “Sangria Sunrise” 10% off Charters
I cannot say enough about how much we enjoyed our stay at Sangria Sunrise! The condo itself is beautiful, the property is awesome, well-maintained, and the staff are friendly and helpful! We spent most of our time at the pool and the beach. The pool bar is great and the pool is clean and refreshing. Plenty of sunny spots and lots of shaded tables, too. It’s right across from the condo so we went multiple times a day. Beautiful landscaping all around. The beach and marina area are really nice. We loved watching the boats from the balcony and seeing the sunrise over the water. Lots of fun things to do in the area within a short drive, but also plenty to do on the property if you prefer to stay put. Tracy is an excellent host and is very helpful and responsive. We will absolutely be back. Thank you for sharing your space with us, Tracy!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!

🏝 Oceanfront Paradise Awaits You
Great place, adorable beach and plenty to do in the area. Home is perfect and has everything you could possibly need for a short stay.

Tropical Escape | Sea Gulls 407 ~ Weekly Rental
We enjoyed our stay in this lovely condo on the ocean side with access to kayak. There is a wonderful and large pool with great seating and shade on property. Many additional fun spaces to explore. Our space was clean, neat and easy to use. It's private and well maintained. Definitely on our list to consider for a future visit.
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
- Cannon Beach
- Biscayne National Park
- Conch Key
- Calusa Beach & Loggerhead Beach
- Theater of the Sea
- Everglades Alligator Farm
- Cocoa Plum Beach
- EAA Air Museum
- Far Beach
- Sea Oats Beach
- Horseshoe Beach
- Monkey Jungle
- Deering Estate
- Windley Key Fossil Reef Geological State Park
- Keys' Meads
- Long Key State Park