Guest house holiday rentals in Winter Haven

Perfect place for a private getaway, perfect distance from the parks. Shanti always responded quickly & made the process super easy going & accommodating. Would stay again 😊

Our stay in Megan’s cottage was everything we needed for a home away from home. Megan was extremely responsive and helpful. Would definitely stay here again 🥰

We loved staying at this beautiful lakeside getaway. It was perfect. Amanda's attention to detail to make it truly a home-away-from-home was spot on! It was peaceful and super comfortable. This is THE place to stay when we come and visit our friends. Our friends are even going to recommend it to family and friends when they come to visit, as well! Thank you, Amanda.

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

Wonderful little getaway for my husband and I! We will definitely be coming back and staying here!!

What a gorgeous place! Jill was super responsive to all my questions (I had many!) and the stay was perfect. We were there for our daughter’s wedding and had lots of coming and going but we felt like we had ample privacy and didn’t feel like we were bothering anyone. The guest house is right on property but not attached. It was perfect!!!! The value was tremendous for the amenities vs.what we paid. We will definitely book with Jill again if we have the opportunity.

A lovely little space! It really exceeded my expectations for the affordable price. Everything was clean, the decor was homey and modern, the kitchenette had everything I needed.

Great, private studio apartment. very affordable, clean, friendly owner. If I travel back to Lakeland I will rent again for sure.

Had a wonderful stay ,it was very convenient to restaurants and stores, place was great and roomy and perfect for the two of us, very clean and very private ,Mariana checked in on us during the stay and was flexible with a later check out due to my train being delayed , I visit Lakeland often and I will definitely rebook again if it’s available! It was super nice!

Absolutely amazing stay! The apartment was incredible — spotlessly clean and had everything we could possibly need for a comfortable and relaxing vacation (and more!). Every little detail was thoughtfully taken care of. The hosts were extremely welcoming and kind, always ready to help with any questions. And the private pool is the best and my favourite part of the whole trip! Highly recommend this place — you won’t regret staying here!

Ron is a great host. He is very kind and I felt safe and welcomed, even bringing our 60# dog. You will feel at home while here. The bungalow and the deck is in it's own area, it gives privacy. The bed was purposely made comfortable (5/5) and the installed a/c unit made the area cool. He provides 2 induction cooktops that work great! We will check for availability when we come here again.

Thank you for a wonderful stay in your Casita. It was very clean and cozy and my children felt right @ home. It was spacious and clean and the A/C was nice and cool. That was very important due to the 100• weather outside. I was able to get them to their Summer camps effortlessly and they enjoyed being there. Thank you once again for an awesome spot to stay on Lakeland.

Maria’s home was perfect. She had all the necessary amenities we needed to make our stay perfect. The home was spotless and comfortable for my family. We will surely book with Maria in the future.

We came to Lakeland to visit friends and had a wonderful stay in this super spacious, comfortable and clean home. Our friends came to dinner one night and we found the kitchen well equipped for cooking. The beds were comfortable and we had plenty of towels. Good location. Helpful and responsive hosts. A very nice stay.

I really enjoyed my stay at Walter’s place and would stay there again. Very scenic, clean, private, and safe. Walter was a great host, very friendly and personable. He treated me like a friend.

The property boasts an exceptional location and a private loft, providing a secluded and exclusive living experience.

Christopher was extremely responsive and the rental was well-decorated, clean, and had all of the tiny details (extra hair ties in jars in the bathroom, new towels, bubbles and a few snacks for kids) that showcased the care that goes into making guests have an excellent stay.

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!!!

Had a nice stay. Location is good to drive to disney world or universal. House is clean and as described. The host is very responsive and kind.

2nd time staying and love it, cozy and a home away from feel. Definitely 10/10