Guesthouse 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 🥰

What a wonderful place, like something out of a fairytale! 🌟 The beautiful nature around is breathtaking, and the inside of the house is extremely clean and cozy. 🏡 The host was incredibly helpful and friendly. 😊 Getting there was a breeze thanks to the clear instructions. 🚗 The spectacular beach offers a spot to enjoy a morning coffee and plenty of fun with kayaking and paddleboarding throughout the day. 🏄‍♂️🌊 Highly recommended! ⭐️

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!!

Monica’s Casa Azul is a cozy, quiet place with bright, cheerful interior and a nice private outdoor area.

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

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!

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.

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.

If you are looking for a very relaxing quiet little getaway. Ron’s is it. Treats you like family and is available for all your needs. I will definitely be coming back when in the local area.

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.

Very easy entry and super clean space, definitely worth the trip!

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

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!