Guesthouse holiday rentals in Winter Park

Can't say enough about this charming house. Guests absolutely loved it! Definitely our go-to for the next show at Clarcona. Look forward to seeing you then.

We had such a lovely stay! Space was super clean, spacious, and full of natural light with beautiful high ceilings. The walk up to the guest house was charming and peaceful too. Really enjoyed our time here! 🏡

I had a great stay at Muriel's place. The spot is only a block off the water, which provides great backdrops for walks. It's a private spot that's conveniently located (not walkable, but only a 5-minute drive) near to the park neighborhoods (Thornton, Audubon, Winter Park, College Park), Mills 50, and downtown. The neighborhood is very quiet and safe with easy access to I-4 and 17-92. This is a great, clean, and well-maintained spot, with a great host, that is well worth the price.

Cute, cozy place with a pool. Perfect for a couple, close to everything. Hosts were friendly and responsive.

This cabin is absolutely perfect! While it is centrally located and only a block away from a busy street, it is very quiet, peaceful and relaxing. We didn't hear a since dog, person, music or car. The cabin is very bright, the kitchen is VERY well equipped, and there are lots of towels, blankets and pillow. (We have stayed at Airbnb's with only 2 thin pillows, 2 bath towels for multiple nights and no kitchen towels.) The decor is eligent, simple but beautiful quality. The cabin is very spacious and highly functional. The host is kind and responsive. This is one of the very best Airbnb's we have ever stayed at and we have stayed in many. A+++

Terry was a great host, and very responsive to messages. Very easy to check in and out of with very clear instructions. The place was clean and tidy, and very quiet. It was a great place to stay! It's also very close to everything downtown!

quiet location surround by a busy area. lots of stuff do do in the area but it was nice having a quiet place to come back to. I really enjoyed having the screened in porch

We loved our stay. Beautiful place, very quiet and private. Clear instructions, easy check-in, place was very clean and comfortable. Right down the road from Yellow Dog Eats which was fantastic. Thank you Noga!

10/10 best place I have stayed in, would recommend

place was very clean and pretty spacious for a 1 BR. The layout was nice. Javier was very chill and was understanding. The bed room was very nice as well.

Let us book last minute! Super peaceful and private. Looks even cuter in person

I loved our stay at genesis air bnb it was very clean and very comfortable. I would definitely stay here again it actually was one of the cleanest Airbnbs I’ve stayed at. Genesis Airbnb get a 10 out of 5 for me 👍🏽💯

Beautiful and peaceful home. Was very clean and private. I would 100% recommend here. I will definitely be back. Allowed me to check in early.

We loved our stay at Leon’s casita. Peaceful neighborhood and convenient to everything College Park and Winter Park have to offer. It also has easy access to I-4. The place was super clean, and well lit with beautiful decor. They provided starter toiletries, snacks and water. Kitchen and bath had all the necessary amenities for a great stay. Will definitely be staying here again on future Orlando visits!

The cottage was perfect for our weekend visit. It was immaculate, very nicely decorated and comfy. We enjoyed the family of Sandhill Cranes that came to visit both mornings and the view of the lake. Our girls were camping at Wekiva Falls RV Resort, so we didn’t do any cooking at the cottage, but everything was available if we had chosen to do so. We enjoyed visiting downtown Sanford as well. Great place!!

We booked this space for a sisters getaway and it exceeded our expectations. The space was calm and relaxing and Verna was very responsive when we asked about bug spray or pool floats. Overall great experience :)

Me, my wife and our best couple friends went to get away for a few nights to just hang out! This place was amazing. Miriam and Ishmael were super responsive and friendly even bringing us eggs from their chickens! Their home is beautiful, pool is lovely and property is amazing! Honestly felt like a little home away from home or that I was staying at my grandparents house, which is an odd thing to be able to say about an Airbnb host. Super grateful for this place and will definitely go back! Dollar General five minutes around the corner that is actually really nice! The area is beautiful. You will love it.

The listing was very cozy and suited myself very well. I will be recommending to anyone looking for a place to stay that is close to any concert venues:)

Had more than what we needed and was a great spot to recharge from the daily adventures we had. Would book again if in the area.

Me and my wife really enjoyed ourselves at this beautiful peaceful property for our first time in Orlando. She was very friendly and helpful also. Definitely recommend!!!

Perfect place, perfect location, perfect experience. Thank you for the excellent hospitality David. We felt at home during our stay and had a great time enjoying the amenities. 100% recommend. Respectful and trust worthy host. Clean space

The tiny house was a beautiful place to stay. It is cozy and it really feels like home. The place was as big as we needed it to be, and perfect for my partner and I. I would 100% recommend if you are looking to stay near the Downtown. If I ever decide to visit Orlando again, I would love to stay here. Everything was clean and very beautifully decorated.

Had a wonderful and peaceful stay. Great neighborhood. Safe, quiet, and beautiful. Plenty of space and super comfy bed! Nadeem is very friendly and makes sure your stay has everything you need! Will stay again.

Our stay at the Guest House was absolutely wonderful! From the moment we arrived, everything was perfectly prepared and thoughtfully arranged. The home was clean, cozy, and welcoming — with lights on to greet us and clear, helpful instructions for everything we needed. Nancy and Richard went above and beyond with the snacks, drinks, and breakfast items, which made our busy tournament weekend so much easier. The grab-and-go options were a lifesaver in the mornings! The property was peaceful and had plenty of space for parking and relaxing after a long day. We truly appreciated the hospitality, attention to detail, and communication throughout our stay. We couldn’t have asked for a better experience and would absolutely stay here again. Thank you for making our trip so smooth and enjoyable!