Condo holiday rentals in Winter Haven

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Popular amenities for Winter Haven condo rentals

Weekly condo rentals

Guest favourite
Condo in Osceola County
5 out of 5 average rating, 18 reviews

V.I.P 5 stars (Disney 15 mns ) Luxury House

BryannaRating, 5 stars1 month ago
Love love love this place! It was perfect for us and we would definitely stay again. The tub is a dream!
Guest favourite
Condo in Kissimmee
4.91 out of 5 average rating, 77 reviews

Coastal Retreat | 15 min to Disney

StacyRating, 5 stars2 months ago
Perfect size for a small family. The pool also great!
Guest favourite
Condo in Davenport
4.97 out of 5 average rating, 29 reviews

Cozy Condo in Champions Gate

DianeRating, 5 stars2 months ago
We cannot say enough about how much we loved our stay during this winter. For the second year we have enjoyed a wonderful, clean, peaceful stay at this fantastic condo. There is nothing to complain about. Ana has been a very responsive and helpful host and everything was just perfect and was truly a comfortable “home sweet home”. We will surely stay at Ana’s condo again and again in the years to come.
Guest favourite
Condo in Davenport
4.89 out of 5 average rating, 36 reviews

Beautiful NEWLY remodeled 2BD CONDO close toDISNEY

Jessica Rating, 5 stars3 days ago
Had a nice time I was a great place and fair price I enjoyed it !!
Guest favourite
Condo in Orlando
5 out of 5 average rating, 9 reviews

Stunning waterfront Views, 1 mile to Disney 2 bath

JayneeRating, 5 starstoday
We were there for a volleyball tourney at the OCCC and it was a great location. Plenty of places to walk to or close driving distance. We also went to Magic Kingdom and Animal Kingdom and it was a good drive to both locations. The pool area was nice - although we didn’t get to really enjoy it because we were at the tourney. We would highly recommend and would book again if in the area. Hosts were very responsive and made sure we had everything we needed.
Top Guest favourite
Condo in Davenport
5 out of 5 average rating, 93 reviews

Resort-Style Townhome with Golf Course View

ShaunaRating, 5 stars1 month ago
I stayed over Easter with my three sons ages 13, 13, and 11. The communication was outstanding, easy check in with a code and parking permit to access the community. We were offered an early check in but our flight arrived later in the day so we weren't able to take advantage but appreciated the offer. The unit is immaculately clean, everything you need is provided, and all the linens and furnishings are in wonderful condition and very comfortable. The kitchen was well-appointed and tons of seating. My personal favorite part of the stay was enjoying the screened in porch area. It is so peaceful and quiet. We watched the sunrise every morning and the fireworks from the Magic Kingdom every night. Having access to the resort amenities was also wonderful and we used both pool areas frequently. The boys also enjoyed the basketball courts and soccer fields. Highly recommend and would definitely stay here again next time I'm in town!
Top Guest favourite
Condo in Davenport
4.92 out of 5 average rating, 53 reviews

Ken & Tanya's Tropical Retreat (near Disney Parks)

JorgeRating, 5 stars1 day ago
stayed with friends and absolutely, love the place great view, comfy, Very clean, beautiful space And so much more, I would highly recommend people to stay here and also I would love to stay here again.
Guest favourite
Condo in Four Corners
4.94 out of 5 average rating, 53 reviews

Orlando Family Retreat – 3BR Near Parks

Oliver H.Rating, 5 stars4 days ago
Accessible to grocery and eateries, clean, and quiet. While not handicap accessible (2 flights of stairs), this safe, secure, and spacious stay in suburbia was a welcomed reprieve with moderate water pressure, gorgeous views, and amazing resort-style amenities. Our host David was attentive and responsive to all concerns. Would stay again.

Pet-friendly condo rentals

Top Guest favourite
Condo in Champions Gate
4.85 out of 5 average rating, 278 reviews

Magical Champions Gate 3/2 Tuscan Penthouse

RominaRating, 5 stars1 month ago
The apartment was super nice! The complex was good, we enjoyed the pool and the jacuzzi. Thanks very much we had an amazing stay.
Guest favourite
Condo in Poinciana
5 out of 5 average rating, 13 reviews

Orlando 3BR/2BA/4BED Beautiful modern amenities

ZlatkoRating, 5 stars2 months ago
We had a wonderful time staying at Ilce’s place. The house was clean, comfortable, and had everything we needed. Ilce was a great host, and we would definitely stay here again.
Superhost
Condo in Davenport
4.8 out of 5 average rating, 20 reviews

Tuscana Resort,Disney a 17 minutos

AngieRating, 5 stars2 weeks ago
This is the first time where I actually am overly satisfied, not only was this home beautiful but it felt like a home away from home. My family and I watched movies and played board games. This home was not only in a super local area we also drove maybe 30 minutes to the nearest outlet mall and had a great time. We also enjoyed the universal themes parks as well !! Great stay would definitely recommend 10/10
Guest favourite
Condo in Kissimmee
4.94 out of 5 average rating, 117 reviews

3 Bedroom w/large patio on Resort Golf Course

PhillipRating, 5 stars2 weeks ago
We definitely enjoyed our stay and maybe some time in the near future, we will return.....
Guest favourite
Condo in Orlando
4.99 out of 5 average rating, 139 reviews

Serene Lakeview By DisneyWorld -Universal Stds 8mi

CarrieRating, 5 stars1 month ago
Adir's place was fantastic. There were many personal touches that made it feel more cozy, which I've found in Orlando can be a struggle. I loved how there were cozy blankets, bathrobes, and a few treats when we arrived. The location is awesome. Very close to anything you could need, Disney, Universal, and the airport. Dollar Tree, Starbucks, Dunkin, Chick-Fil-A, Walgreens, and many more places are all within walking distance. I loved how peaceful the condo and location felt, despite being surrounded by everything. The view was beautiful to wake up to and my kids enjoyed playing in the pool. We would definitely recommend and be happy to stay again!
Guest favourite
Condo in Celebration
4.9 out of 5 average rating, 112 reviews

Pet Friendly in Orlando Area near Disney.

HannahRating, 5 stars1 day ago
We loved our stay. The pool was so fun for our one year old and we were able to bring our cat on our trip - and he loved people watching out the windows! It was clean, the hosts were responsive, and the pool/surrounding areas were so much fun. We will definitely book with them again if we go back to the area!
Superhost
Condo in Kissimmee
5 out of 5 average rating, 3 reviews

Pet Friendly Reunion Condo Minutes from Disney!

HeatherRating, 5 stars4 months ago
Amazing little spot if you are in the Orlando area. Pristine air b&b. I walked into a freshly clean condo with soft music playing on the tv, lights turned on and a plate of snack waiting for me. Communication was wonderful and the door was peaceful and homey. Absolutely would stay here again.
Superhost
Condo in Four Corners
4.72 out of 5 average rating, 120 reviews

No BNB fees -Oasis Condo 5 min to Disney

SoniaRating, 5 stars1 week ago
Very beautiful location, calm surroundings and very close to all attractions

Condo rentals with a pool

Guest favourite
Condo in Davenport
4.86 out of 5 average rating, 49 reviews

2BR Bahama Bay | Pools, Beach, Sauna | Disney

GlendaRating, 5 stars1 day ago
Very nice and quiet place, everything was cleaned and ready for us to enjoy our stay. We enjoyed the pool and will definitely will be coming back.
Superhost
Condo in Davenport
4.76 out of 5 average rating, 68 reviews

Lovely 1 Bedroom Apartment with Pool and Jacuzzi!

TinaRating, 5 stars1 month ago
Perfect stay! Clean, accommodating and everything near by!
Guest favourite
Condo in Davenport
4.92 out of 5 average rating, 72 reviews

Gated resort minutes from all major attractions

MekiylaRating, 5 stars1 month ago
Very spacious, clean , free of excessive clutter. I loved the items for an infant/toddler. (I brought my 10 month old). It was perfect for my small family. A responsive host a well equipped kitchen and it’s close to a lot of restaurants. Overall 10/10. Will be returning.
Top Guest favourite
Condo in Davenport
5 out of 5 average rating, 54 reviews

Aqua Dream > Tropical Bahama Bay Condo Near Disney

DaliaRating, 5 stars6 days ago
Spectacular!!! This was by far the best airbnb we have ever stayed in. Well decorated, furnished and filled with everything you'd ever need. Lots of fun to do around the resort. Raymond & Kevin were very responsive and helpful. Looking forward to booking with them in the future.
Guest favourite
Condo in Kissimmee
4.79 out of 5 average rating, 187 reviews

Mickey's Retreat(K2)

JackRating, 5 stars1 month ago
Stayed at Celso’s apartment for 2-weeks. It was a great size for 2 people and an ideal location for those looking to do the Disney and Universal parks. Apartment is just a short drive away from plenty of shops, restaurants and fast food places. It also has a 24h petrol (gas) station just outside of the complex which is really convenient. Overall, really enjoyed our stay the complex is really nice and feels very welcoming. Would highly recommend for two people. Celso was a great host, super responsive to any messages and helpful with any questions we had during our stay. One minor downside, not to the fault of Celso or his apartment, but the complex had a nesting hawk during our stay. This was no issue for 95% of our stay, but did swoop at us once. Would advise being cautious when walking to the car park, especially with young children.
Guest favourite
Condo in Orlando
4.97 out of 5 average rating, 93 reviews

Modern Lake view Condo 1 mile from Disney

AniaRating, 5 stars1 week ago
A wonderful stay in Orlando beautiful view and the condo is super clean and cozy me and my boyfriend enjoyed our stay and it was in the perfect area plenty of dinner spots and fun activities close by you will love this place and I will make sure to book again my next visit to Orlando
Top Guest favourite
Condo in Four Corners
4.97 out of 5 average rating, 36 reviews

Condo Near Theme Parks!

DanielRating, 5 stars2 weeks ago
great place. I really liked that the kids room had toys for my child to okay with. he loved the bunk beds and the themed rooms. House was great and had everything we needed. Location is great and the community has things to do there aside, great for a rest day from going to disney
Guest favourite
Condo in Davenport
4.94 out of 5 average rating, 54 reviews

Home Sweet Home

IanRating, 5 stars2 weeks ago
Blancas place was definitely a great choice for us. We stayed here with 3 guests and it accommodated all of our needs; from having the indoor washer and dryer to a little work space for computer work. My group stayed here for our 3 day Disney trip, we still drove a little over 20 minutes to get to the parks but that was not an issue for us as it seemed like we weren’t really getting hit with terrible traffic whilst driving to near by stores or restaurants. Very close stores and restaurants less than 10 minutes from the place. Pool and hot tub were super nice. AC worked almost too good inside the space lol we had to turn it up a couple of times because we were freezing. Space was overall very clean and nice, the only thing I would mention is there is no BBQ/ grill however it is listed in the amenities. Lovely space and definitely will be booking here & with Blanca again in the future !

Quick stats about condo rentals in Winter Haven

  • Total rentals

    10 properties

  • Nightly prices starting at

    $100 NZD before taxes and fees

  • Total number of reviews

    50 reviews

  • Wi-Fi availability

    10 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

  • Local attractions

    LEGOLAND Florida Water Park, Winter Haven Hospital and Harborside

Destinations to explore

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