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

Cancellation Deal: 08/02 thru 08/09
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie

Waterfront Home 37.5-ft dock, Cabana Club Included
We were very comfortable at the home during our week stay. Great place to stay if you need room to park a boat trailer. Quiet very nice safe neighborhood.

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

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.

Cary’s Oceanside
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Apartment rentals with outdoor seating

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
Norma was the most responsive host I’ve ever encountered. Her replies were prompt and she provided outstanding recommendations for local restaurants and entertainment. She checked in with us frequently. Her rental is adorably nautical, clean and well-maintained. I loved her style! She made sure we had everything we needed.

Seaside Vista - Ocean Front 2/1 with dockage
We had to make a very last-minute booking for a two-night stay and were thrilled to find this boat- and pet-friendly spot with space to park our boat trailer. Justin was incredibly quick to respond and made the whole process seamless. The accommodations were clean, comfortable, and exactly what we needed. There was more than enough room for our 24-foot boat, which stayed well-protected from wind and waves. A freshwater hose was conveniently available to rinse the boat off after a day on the water, and the on-site fish cleaning station was a great bonus. The property is just three doors down from Snappers Bar & Grill, where we enjoyed live music, great food, and drinks. We even had the pleasure of meeting the property owners during our stay—truly some of the nicest people you could hope to meet. Overall, a great stay. We’ll definitely be back!

Turtles Nest 2 Ocean Point condo
Had a fantastic stay! The home is very nicely decorated, the beds were super comfortable, everything was nice and clean. Of you intend to hop around to the different parts of the keys this is a good location in between everything. Very peaceful, safe, and easy to find and access.

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

Beachfront Condo w/ Ocean Views in Marathon
This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.
Condo rentals with outdoor seating

Your Happy Place - Oceanfront
Sandra's place was very nice and clean. She was very reponsive with any and all questions. The accomodations are as listed. I enjoyed the peace and quiet. I most enjoyed relaxing on the balcony listening to the ocean. All you need is you, clothes, and the memories you will make. The rest is provided. However I will note that I was expecting a "real" beach and it was more of a lagoon. although still nice. Thanks Sabdra I would definitely book again. 🙂

2BR - Key Largo Sunshine Getaway
We had a wonderful 4 night stay here. Condo was VERY clean. It had everything we needed. Good location to get to many other places. We took a lot of day trips and excursions. It turns out, my kids liked our time at the community pool the best! Thanks for the memories. The only downfall was the mosquitos were terrible at night. Bring bug spray. Obviously not the owners fault. We had a great stay for 5 people and would come back again! Thank you.

Key Largo Baha Penthouse Ocean Pointe 1416
Great hosts. We had a little trouble figuring out the electronic locks, but they responded almost immediately each time we reached out to them and were very helpful.

Waterfront Spacious Condo Key Largo #4, 10% Off 7+
Great stay and communicative host. We stayed for a wedding nearby and this was a very clean and quiet place to stay

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!

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
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.

Tropical Getaway
We had a great stay at Kawama, Key Largo Everything was as described in the listing and photos. Great location, good facilities with the pools, creek and beach options. We enjoyed sitting in the shade by the beach having a drink and snacks as the sun went down. Also really handy for snorkelling at John Pennekamp. Would highly Recommend Many thanks Gladys!
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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
- Everglades Alligator Farm
- Theater of the Sea
- Cocoa Plum Beach
- EAA Air Museum
- Horseshoe Beach
- Sea Oats Beach
- Monkey Jungle
- Far Beach
- Deering Estate
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads