Beachfront holiday rentals in Windley Key

Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.

Thank you Frank for a great place to stay! Close to restaurants, quite neighborhood, nice pool, a dock to swim and fish from, and beautiful sunsets. We had everything we needed.

We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!

We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!

Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.

We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.

Maidelin was very communicative with us to ensure we had everything we needed and to provide instruction or local recommendations. My only complaints are about the region and not Maidelin or her property. "Beaches" are rare in the Keys so don't expect waves or traditional beaches. Maidelin's place does have a sandy spot adjacent to the water next door to her, and residents didn't seem to mind sharing the space. The backyards are more shared than private, so you'll see people walk by from time to time. You'll also see iguanas, birds, other lizards, and fish! The nature of this type of property puts tenants extremely close together. Porches share railings and windows sometimes face other homes' windows. Walkability is pleasant through the shared resort area, but there's very little in the way of food or retail that's walkable. A 10-15 minute drive to Marathon though will get you what you want. Overall, a nice place to stay, but especially if you want to stay out of the more popular Keys.

Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!

Our stay was everything we could have wanted. The view was incredible. The condo had everything we could need. We will definitely come again and recommend it to family and friends.

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!

First RV experience, did not expect massage sofa... everything you need to explore the mangroves off the beach, take a paddle and who knows what you'll meet...explore the state parks, snorkel, dive kayak fly...it's what you make it ..wish we were here for longer and Kelly is a top host...🤗

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.

Martha was super helpful and responsive. The place was very nice, clean, and had incredible amenities. Kids loved it!

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!

This stay was close to absolutely everything you’d want to do and see in Islamorada! The host was friendly, provided easy instructions and a home that felt like home. Was glad to find this amazing, cozy space, will be back soon.

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.

The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!

Pedro was an amazing host! We got in a little early and thought we were going to need to check in early and he was very accommodating! I had a few questions and he responded almost immediately which is more than impressive! The place is perfectly decorated, had a very homey feeling to it and everything we needed.

Loved it! I hope to go again some day in the near future.

Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!

Amazing location, great house with lots of space, cute artistic touches and we really appreciated the sharp knives! The screened in lanai was fantastic! Highly recommend! We’d come back in a heartbeat!

Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Great place. Absolutely gorgeous views. Hot/pool was wonderful and refreshing. Would absolutely recommend this place.