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

Cozy, Relaxing & Fun Gateway!
I really enjoyed my stay here with my husband and 3 of our children. The home was clean and ready once we arrived and she was feline with our checkout, which we greatly appreciate. We felt really welcomed and appreciated her communication skills and hospitality!

15% Off Florida Summer Vacation Rentals
There is so much to be said about this property! Beautiful home! Beautiful view of the lake! Accommodations better than pictured! Full kitchen with every appliance and great quality. The master bedroom bed was as comfortable as our home bed! The bedding was great quality! We will be back to this property!

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..

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!

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

Breathtaking Home
I thought the place was great, the kids loved the pool in the backyard. This was drivable to Disney which we opted to do for a few days and Jennifer was always so responsive. There was some live music across at the community pool but I didn't think it was overkill and the kids slept right through it. I will rent again.. hopefully soon!

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!
Family-friendly house rentals

Luxury near Disney Large extended private pool/spa
It was a very nice home and plenty of room for the 9 of us. The kids really enjoyed the pool and game room, but the video game system did not work. It was very clean and insect free. It was a very nice neighborhood with beautiful views. We meet a very inquisitive racoon that was looking for food, but we didn't provide any and always made sure the garbage was secured. We named him Denny the Disgruntled Racoon. Recommended additions would be a blender. Also, make sure you bring extra toilet paper, paper towels, dish detergent and garbage bags if you plan staying here. Beds were comfortable. Overall it was a great place!

3 bedroom Villa in Kissimmee
I cannot say enough good things about Raymond & our stay. I travel a lot for my son’s lacrosse team & this was our favorite Airbnb so far! Raymond is very responsive & kind! I hope it’s available to book next year when we return.

The Old Haven - An Enduring Piece of Nostalgia
Great location. Easy access. Hosts were great with communication. Would definitely book again.

Disney World Area Villa Orlando * Pool * Sleeps 10
We stayed here for 3 weeks and had a lovely time. The house itself was well equipped, especially the kitchen, plenty of towels, loads of TV channels to watch and very close to all the parks and amenities. Had a great time thank you.

Luxurious Private Retreat w/Spa & Saltwater Pool
Carrie thank you so much for hosting our family! This was so much better for our family than a hotel! Our kids never said they were bored! The next time we are in the Orlando area we will book again for sure!

Beautiful 5 Bed Home With Rear Conservation Views
Fantastic stay in this beautiful home. We have rented before in Florida and this was outstanding. Well equipped, clean and very peaceful around the pool with a nice outlook. Lovely shared pool on Watersong which was very peaceful with well kept gardens. Gary was an excellent host who was very helpful from the day we booked it and I would have no hesitation in recommending. It was an hassle free 2 weeks which is just what we needed.

Amazing 4 bed home, large pool, Disney 12 miles!
This place was perfect for our family very spacious and open the safety of the pool and pool alarm was awesome! Quiet private area near everything would absolutely recommend to anyone

Orlando 5BD+Pool, Near Disney & ChampionsGate Golf
Just want to say it was a great stay !!! The house is very nice just like the pictures !!! Our host was fast at responding any of our questions I would recommend to anyone to stay here you will not be disappointed!
House rentals with a hot tub

Modern 3br home
Listing is very accurate. Comfortable furniture and beds. Exceptionally clean. Close to everything we needed on our trip to Legoland. Highly recommend

Lake Whistler Beach House with lakefront pool
Very rarely do you find an Airbnb that super-exceeds your expectations. This home absolutely did that. Everything was nicely appointed, yet warm and homey feeling. We stayed as 2 adult couples and had a great time. That said, if you're a family of 8, you'll likely have a great time as well. The game room was a lot of fun, the kitchen had everything you'd want to cook inside or out. The pool was perfect sized, clean, and we'll kept. The grounds were beautiful. The lakeside area was awesome. literally zero complaints other than hating to leave.

No Airbnb fees!Themed Home Pool/Spa/Gameroom 21811
our stay was amazing! host was very responsive and fast. the home was beautiful and my kids and family really enjoyed it. loved they had a crib on site and ready to use. the location is perfect everything super close and easy to find. had all the basics we needed to start our stay. would def tell our friends and family to stay there! 10/10!

PRIVATE Pool Villa - Family Holiday Getaway
The villa is in a great location, 10 minutes drive from shops for groceries and restaurants. We had everything we needed and the kids loved the pool. Richie was quick to respond to any questions we had. Beds, sofas and loungers all really comfortable

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!

There is no other place you want to be than here.
Franks place was perfect, everything in the pictures was accurate plus so much more. We had everything we needed to start and then some, we didn’t feel like we needed to unpack and go right to the store. We spent most of our time out at the pool and with small kids the door alarm, took some getting used to but was such a nice touch. Plenty of restaurants and grocery stores near by and only about 30/40min to universal. We would stay here again in the future, the place had so much space we never felt like we were cramped in the home.

Southern Dunes Lakeview Poolhome
We had to unexpectedly extend our vacation and this place was perfect. Jeffery was kind and responsive. My kids loved the toys and pool. Having Walmart right around the corner was perfect! The community was quiet and lovely. 10/10 recommend!

Stylish Villa Private Pool-SPA Near Parks Disney!
We had an amazing stay at this beautiful home! The house was spotless, spacious, and even more stunning in person. The pool and hot tub were absolute highlights and made our trip feel like a true getaway. We felt comfortable and relaxed throughout our entire stay. Highly recommend!
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
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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