
House holiday rentals in Winter Haven
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Top-rated house rentals in Winter Haven
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Popular amenities for house rentals in Winter Haven
House rentals with a pool

Awesome Vacation Home w/ Private Heated Pool/Spa
We had a wonderful short stay in Orlando. The house was peaceful and relaxing after long days at the Disney parks. The pool was perfect and the outdoor dining and furniture were really nicely designed and comfortable. The house has everything you need to feel right at home. Lovely soft towels and linens. A great laundry room and games room. Wendy our host was so thoughtful and descriptive in the pre arrival communications, so we felt very organised before we arrived and during the stay we had a direct communication with Ron if we needed anything (we didn’t, but it was reassuring to know we had someone to call if needed). I will definitely recommend the home to friends and family looking for a place to stay during a trip to Orlando. Thanks for having us!

Stunning 4BR home w/Pool
I was very well pleased with the stay. The pool was nice and warm. The surrounding was peaceful and quiet. I really would love to come back again. Also, the cleanness of the house was excellent.

Spacious 3BR+Den with Pool, Near Disney & More
Hi the stay at Dan and Emilias lace was wonderful, it was spacious, clean, near stores and restaurants, great place, thy had it well equipped with everything you will want and need ,it was like you were at home for real, I'm a cook and the kitchen had something I needed , they even had a hand mixer, cutting board, all sizes of bowls, and ots and pans, we really enjoyed the stay, THANKS AGAIN..WE WILL COME BACK..

Luxurious Golf Front Oasis: Pool, Spa, View&Cinema
We had such a great time staying at Michael’s place! Our five teenagers were never bored with all of the fun amenities! The kids had a great time with the karaoke machine, arcade games and outdoor area! My husband and I love coffee, so we really appreciated the coffee bar and supplies that were provided. The house was beautiful and Michael was extremely responsive. We would stay again!

4/2 New Spacious Pool Home
Everything was great. Home was fully stocked with everything you and your family may need. My babies enjoyed the pool and Lego room. If we’re ever in this area again, I would definitely book with Rachel!

Heated Pool | Luxury Design | Disney | Golf Course
Our family (2 adults and 2 kids under 10 yrs) enjoyed our week long stay. There were a few things that needed attention with this property. I communicated those with Lukasz and he was responsive. I am sure those will be taken care of quickly. Some thing to note is that this property does back up to the golfing fairway. They grounds keepers will be out before dawn mowing and fertilizing before those early tee times. The machines are muffled and you can tell that they try their best to not distribute but you can hear them. It never disturbed our kids but it did wake the adults. If you are a light sleeper or like to sleep in, that may not be great for you. This being said, we LOVED the house, pool, hot tub, outdoor patio and everything that it had with it. The kids enjoyed the themed bedrooms as well. The short drive to Legoland was perfect. We went to a few parks in Haines as well. We would stay here again without question.

House, backyard on the golf course Park Place
Michel's villa in Haines City is amazing. We had been let down by a booking at another AirBnB which didn't match up to the photos and fortunately Michel's place was available for us to book instead. We were so relieved to discover that the pictures of Michel's place were accurate and perhaps didn't do it justice for how beautiful the place actually is. The villa is beautifully presented and equipped, everything is in working order and we had everything we needed. The villa is on a gated community alongside a golf course. The process for gaining access to the neighbourhood at the security barriers was quick and easy. There is a large Walmart nearby which was ideal for buying any supplies we needed during our stay. There are also plenty of restaurants/takeaway options in the area such as Manny's Chophouse and Floridinos. Overall we would rate the stay as 10/10 and we would consider staying here again. Thank you Michel!

Luxury Home 4/3 near Disney, 2 Masters
The home was beautiful, walking up the the home the directions to enter the home was very easy. Opening the door the house was very clean and smelled refreshed. Bedrooms were good size and the private pool was a big hit. My kids enjoyed it and there was alot of pool toys and life jackets for the little ones. The kitchen had alot of cookware. In the playroom were beach toys, strollers and even highchair which helped my babies. Game room had plenty of activities for all ages of kids. Laundry room was very helpful as well. Doug was responding quickly was amazing! They had a book with all information regarding home, rules and people to contact for major needs. My family and I had the best family vacation and we couldn't of done it without Douglas and Kathy. HIGHLY recommend staying in their property. Can't wait to come back and visit.
Weekly house rentals

"Elohim Cozy House" In Winter Haven
Me and my friends enjoyed our stay at George’s home for our weekend in winter haven Florida the home was clean was in a good quiet neighborhood we would most definitely be booking again .

Lakeside Bungalow - Winter Haven Chain-of- Lakes
Recommend, felt like home friendly host loved the landscape and lake view very clean will stay again

BlockHaven near Legoland, Disney
Sayli did a good job in arranging the house. The instruction was clear and the communication was efficient and smooth. Each room is are cozy with all the necessities. The kids like all the Lego/ Peppa-Pig elements around the house, which made them feel home and relaxed. The location is relatively convenient to Legoland and Walmart. The experience of this stay was pleasant. Thank you, Sayli :)

Lakefront House w/ Private Pool, Beach & Dock
We had a wonderful stay and would love to return! Very clean and comfortable. Lots of amenities and activities, making for a perfect stay! ✨

Executive home on private lake.
I must say that we really enjoyed our stay at the home ..it was like home away from home all the amenities were great, the home is much larger and spacious than what the pictures shows. The area was peaceful, we had no issues. The home was clean and the Host Hospitality was absolutely amazing and stocked with everything a family needed or could ever ask for. We didn't really get to use the pool but it looked very inviting. if ever in the area my family would stay again, over all a great place to stay..

Winter Haven Legoland Retreat
Excellent location, cozy feel & very easy check-in. I will definitely consider staying here again with my family in winter haven.

Lakefront Home on the Winter Haven Chain O’Lakes!
We had an amazing stay at this beautiful property right on Lake Roy. The views of the water were absolutely stunning, and we loved having direct access to the lake—it made for the most peaceful mornings and relaxing evenings. The home was spotless, well-equipped, and clearly cared for with love. Whether we were sipping coffee on the dock, kayaking, or just unwinding inside, everything about our stay was seamless and serene. Our hosts were responsive and welcoming, making the experience even better. Highly recommend for anyone looking for a quiet, scenic escape in Florida!

Carefree Cove on Lake Connie - with Hot Tub!
Great place to stay and relax, enjoying the patio, lake, and hot tub. Beautiful decor and home feel on the inside. Master bed slept great. Kitchen had everything needed and more. Will definitely try to stay again, if ever back in the area.
Private house rentals

Cozy, Relaxing & Fun Gateway!
I want to express my gratitude to Jovanni. The house was lovely and cozy. It was spotless, and we had a great time enjoying the pool. Overall, we had a wonderful experience and truly appreciated our stay.

Sweet vacation home.
Needed a place to decompress after visiting Family and this was the perfect spot! We really enjoyed being able to play pool in the garage! What a great surprise! Let’s do it again!

Encanto At Auburndale
This is always our go to place in Auburndale when in town for the weekend. It is always super clean, and it makes it easy to sit back and relax.

Relaxing 3 Bedroom Home with a Pool!
It was great to be part of Liz’s air bnb. My family felt right at home, it was cozy and very peaceful !

Cozy Lakefront Home w/ Pool -7 mins from Legoland
The house in general is fantastic, the beds are very comfortable everything is good but the front yard and the back yard need a little more love to make the house perfect other than that we really enjoyed our stay and recommend the house to anyone who visits Winter Haven

Luxury Tropical Themed Villa With Lake View!
We had a wonderful stay!

Family-Friendly Haven near Downtown - Fast Wifi
Stayed 2 weeks and would 10/10 recommend. The best stay for the price.

Magnolia Farmhouse- Cozy with a Perfect Patio
Our family stayed here for our summer trip to Legoland. The house was perfect for our family of six with plenty of space! It was super clean and had a beautiful outdoor porch area that our family really enjoyed. The beds were extremely comfortable and we all felt right at home. We especially liked the sound machines in each room! The only “issue” was the driveway was small and with the neighbor’s broken fence leaning onto the property, it makes for a tight squeeze for your vehicle. However, the host was amazing at communicating and made us aware of the fence issue ahead of time, letting us know they have gone through the proper channels to hopefully get the neighbors to repair the fence. Overall, the stay was great and we would definitely stay here again!!
Quick stats about house rentals in Winter Haven
Total rentals
290 properties
Total number of reviews
10K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace
Destinations to explore
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- Raymond James Stadium
- ESPN Wide World of Sports
- Busch Gardens Tampa Bay
- Amalie Arena
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- ICON Park