Guest house 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.

I booked this stay for my parents, and they had a lovely time! Great location, wonderful airbnb space!

Great little place in a cul-de-sac. Alvaro was incredibly friendly and helpful. I would gladly stay again.

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!

we had a wonderful stay at the Coach House, it was well set up, clean, and in a lovely neighborhood. the hosts were communicative, helpful, and very friendly. we would highly recommend anyone staying in the Orlando area stay at this accommodation.

We enjoyed our stay very much and look forward to returning again sometime in the future. This is a quaint little cottage in a quiet and very private setting.

unbelievable tranquility hidden in the heart of Orlando

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+++

Wonderful place, peaceful, and a beautiful kitty that hosts the door! Diagones is very polite and attentive :) Highly rexommend

Absolutely worth it!!! Couldn't have asked for anything better at this price point. The host was helpful and responsive and the property was perfect for us!!

Claudia, Thank you for letting us stay at your wonderful place. I thought my message went through about the ac leaking from the grill (onto the kitchen floor) but I just saw for some reason it shows not sent. I used a towel to wipe up the water. No worries about it. I just wanted to let you know what happened. Thank you so very much again. John

This was the perfect spot for my mom and me to stay in Mount Dora. The guesthouse was nicely secluded, and the home was well stocked with all the necessities. We enjoyed our time here.

Everything was on point! What's most important for me, is that there is a desk and chair where I can work on my laptop. Inside was so nice that I almost expected a butler to come with it! Great job!

We had a great stay at the Idle Cottage!! Perfect location- Clean- Quiet- and Comfortable.. We WILL be back !! Local owners who are available if needed and the perfect hosts.. Thank you Sam and Lauren…

Amazing stay! I stay in Orlando about this time every year and this is one of my favorites, the private pool is so peaceful and the unit was comfy and private.

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!!

Sapphire Cottage is the perfect getaway, tucked back off a quiet road , and an 20 minute drive to Mount Dora, making it both peaceful and accessible to town. A canal runs behind the property and there are 2 kayaks you can use if you’re feeling adventurous, if not, you can just hang out and watch the happy hens roam the property or pet the goats in their enclosure. The cottage is really quite lovely, very comfortable, modern yet cozy feeling at the same time. Miriam and Ismael obviously put a lot of thought into its design and decor. The rooms are spacious, the cottage is spotless, and everything works as it should. Miriam and Ismael are the perfect hosts, available yet unobtrusive. I would go back in a heartbeat, and can recommend it without hesitation.

Very nice, well furnished and fully provisioned. Peaceful, quiet and comfortable. Hosts are thoughtful and friendly too.

Great stay and very flexible

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.

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

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!!!

Jill was the most amazing host! The was incredibly responsive, friendly, and truly went above and beyond to make myself and daughter felt comfortable. Everything was just as described. The fully functional kitchen was also the best-stalked airbnb kitchen I’ve ever seen. We had no issues cooking meals. The dogs made me feel safe and secure. I was missing my own dog, so they helped with that. My daughter loved the pool and spent most of the day in it. They also had a beautiful fenced in back yard with umbrellas and plenty of seating with shade if needed. Speaking of keeping cool, the A/C unit works really well! Jill was very responsive and even anticipated our needs multiple times. My daughter insists that we stay with Jill when we come back to Sanford.

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.