Winter Park Rentals with Hot Tubs

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2,101 villas in Winter Park with hot tubs

5Br/3Ba townhome with hot tub/ lake View,Close Disney,Seaworld,Convention Center

Kissimmee townhouse

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$149

The Charming Mickey's Tree House,

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Mickey Mouse Hut” Wonderful home. Everything you need for a home away from home. Pool was awesome. More than enough pool towels to use. Home was very spacious. Only complaint I had was it was not enough cookware to use to cook meals enough for a large group. Other than that small gesture, I give it 5 stars. Thanks for letting us share another vacation in Florida in your home.

Responds fast! avg. 2 hours 46 minutes

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Price per night from

$123

SWISS 56 - Lake Denise

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$295

Gorgeous apartment just minutes to Disney parks, Orlando Florida.

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also liked how there was a patio in back. It made it feel more like a home. We stayed on the top floor where there was vaulted ceilings and lots of windows in the front room. This made it feel more spacious and rich. The amenities were additionally nice as well. There were 2 different pools and jacuzzis, tennis court, clubhouse and work out room to enjoy. I also liked how you could park right up against your condo building. The location was very convieinent as well. It is close to all major attractions. 15 minutes from Disney - 25 from Universal and close to shopping, and restaurants. I would stay here again in a heart beat!

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$125

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great Stay” The house was a better option than hotel rooms. The house was very clean and they had everything necessary for a pleasant stay. They also provided pool towels for the pool or jacuzzi. The jacuzzi was nice and hot and a good option in the evening. Each bedroom had a TV and they had a pool table in the garage. It's a quiet neighborhood. It's not far from Disney or Walmart for groceries.

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$120

Caledonia Lodge - fabulous 5 bed villa nr Reunion

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Love it” me and my family loved this place,kids love the pool me and my wife loved the game room,for peace and quiteand my dauthers love all the space they had.

Responds fast! avg. 1 hour 17 minutes

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Price per night from

$160

1.5 M to Disney,From $100/nt,3BR 1600 sqft Townhome

Kissimmee apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Spacious family friendly condo close to Disney.” Perfect location to visit Disney. Very spacious with a full kitchen . A great family friendly condo.

Responds fast! avg. 1 hour 27 minutes

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$115

Close to Disney,Seaworld,Convention Center,4br Townhome with Hot Tub

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great Family Friendly Home” We had a blast. It felt safe and secure. It was clean and spacious. I have a large family of 9 and everyone had plenty of space. Quiet but friendly neighbors. Amenities were awesome. Hot tub was so relaxing. We had a great time.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$132

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Price per night from

$286

5br/3ba townhome with hot tub,Near Disney,Seaworld,Convention center

Kissimmee apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Vacation rental” The overall experience was nice. The hot was only hot for one day and wouldn't get hot again there after. The cookware needs to be updated but overall we had a great time. I wouldn't definitely rent this rental again.

Responds fast! avg. 1 hour 27 minutes

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$138

“Wonderful vacation” This villa was more than we expected . Great location , easy drive to all parks. Resturants and supermarket close by. Home is very spacious and nicely decorated. Pool and game room a real plus for kids. Home was very clean and well equipped. High chair and pack n play were there and pool Was heated as we requested. Would definelty rent again.

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$252

From $110/nt,4br/3ba townhome with lake view,Near Disney,Seaworld

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$132

SWISS 28 - Lake Stephanie

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$285

Luxurious Villa in Marbella resort, Davenport, Fl

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Birthday Trip” We were in Orlando celebrating my son's 4th birthday and it was great. The house was clean and very maintained. I spoke with the property manager once, and he gave us some great tips for travel and dealing with the heat. The instructions were clear and we enjoyed our visit.

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$206

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

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Price per night from

$206

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$212

Marriott's Royal Palms Resort Orlando Near Disney

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$171

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Price per night from

$228

Beautiful 6 Bedroom Home in Reunion Resort and Spa

Reunion house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 14 minutes

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Price per night from

$486

Sweetbay Villa

Clermont house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great home.” Everything was as pictured. Clean and quiet area close to many restaurants and shopping. Owner was easy to work with and responsive.

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Price per night from

$206

Rainbows End 3 bed & Bath - Florida Villa - Private Pool & Spa

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Better than a hotel” The villa is located in a nice,quite environment but close enough to Disney and to shopping opportunities. It is fully equipped with everything you would need, a lot of entertainment facilities are available. Too bad that the little children costumes in the closet wouldn't fit any of us. We very much enjoyed the calm environment after a long day spent in Disney World. Thanks for the pleasant experience hope we can return some times!

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$160

Disney Pool Home, Great view, Gated resort

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$218

Caribe Cove Resort - 2 BR * Unit Top floor * New Mattress - WiFi/Parking free

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$252

Watersong Resort | Pool & Spa | Games Room 338

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$119

9 Br/6 Ba luxurious Pool House from $380/nt, Close To Disney

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Great time!” House was a perfect fit for my family. We had a great time and plan on making this a yearly trip. Central to everything, but far enough away you didn’t feel trapped. Would highly recommend it!

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$343

SWISS 29 - Golf Course

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$250

Disney World 2 Miles

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$135

Premium 4 BR - Free Wi-Fi, Geothermal Lazy River, Pool, Children's Area, Disney

Davenport hotel apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“very cozy and comfortable” Loved the resort, pool, lazy river. Great place to relax and come home too after a busy day at the parks.

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$126

Amazing house near Walt Disney [UPGRADED!]

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Excellent” Amazing resort! Very clean, comfortable would definitely stay here again! Sandra was also very nice great communication!

Responds fast! avg. 28 minutes

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$143

3Bd Sleeps10 w/ Pool & Close to Disney *Festival 282

ChampionsGate house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$136

SWISS 06 - Lake Sumner

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$295

The Ultimate Florida Vacation

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” Very cozy, out in suburbs. Neighborhood clean and friendly. Pools and outdoor basketball courts and activities for the kids.

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Price per night from

$110

Reunion Resort-luxe 3BR/3BA Villa-Water Park

Reunion hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Terrific Property” Dear Stacy and Craig, What a time we had! Expecting, as many Orlando-travelers do, that the theme parks would be our only major attractions, we were so pleased to be able to add our accommodations to this list as well. The Sagers have made it absolutely impossible for their guests not to have a first-class time in their condo on the Reunion property. And what an amazing property it is! Swimming pools galore (to include my daughter and son's favorite water park with a lazy river) and my personal favorite swimming and late-afternoon beverage/snacking pool area, Seven Eagles. It is here that we were able to really let-down after an amusement park day and relax only to go home to Stacy and Craig's little slice of heaven with beds that beacon even the most restless tourists. I loved the beds! So incredibly comfy with just the perfect linens making vacationers want to stay in bed just a little longer before heading back out to Sea World; Animal Kingdom; the Magic Kingdom, and the the like (all of which are not more than 15 minutes away). A true place of luxury, the Reunion four star hotel is always available to the Sager's guests serving up pub and kid fare all day and night; fine dining; and late night cocktails and sushi on the 11th floor where fireworks from local theme parks are a daily occurrence. Will we go back, yes! In fact, we have already booked again with the Sagers so we can dream away some of those cold winter days and nights looking forward to our next tip down. Thanks to you both for a wonderful stay. Jen and Dan Smith

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Price per night from

$205

8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$343

5 Bed Luxury Vacation Home in Kissimmee FL

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Great home & location.” Beautiful and private, with plenty of space. My family enjoyed our stay here. Loved the location and spaciousness of rooms as well as pool & backyard.

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$252

DISNEY area Vacation Home at Regal Palms sleeps 9 w/Free WIFI

Davenport townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

“Great place!” Loved the area, away from the traffic, very pleasant. Will stay again. Family enjoyed it. Great way to separate older kids.

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$217

Spacious Disney pool home w/ Spa, near golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“PERFECT FAMILY VILLA!” This villa is HUGE and gorgeous! We were traveling with a large family and with 7 bedrooms and 9 beds plus a crib in the master there is more than enough room for your whole family to enjoy a get away! There are 2 rooms located down stairs so if anyone is disabled they can use these rooms. This home is beautifully decorated and so comfortable for us. We thoroughly enjoyed the screened in private pool -with a bathroom entrance right off the pool area! We felt very safe in the community this villa is in and the area surrounding it. Champions Gate is a gorgeous little community with everything you need within 10 minutes. We were visiting Disney and found this villa a wonderful option to staying in the parks. It took us 15 minutes to get to any park and we always parked and loaded a tram quickly and went right to the door. I don't know why people have always convinced me staying of property would be such a hassle..it was no hassle at all! A lovely bonus to this villa was an ice cream truck driver lives right down the street and hits the neighborhood 2 times a day. The kids LOVED that! The home came with all the comforts needed to make us feel at home. Including pool toys, 2 high chairs, iron/ironing board, hair dryers, big beach towels, bath towels and rags, kitchen towels and all the cooking utensils and appliances needed for cooking meals. We did have a dilemma with an odd shape staircase that our child gate would not fit and a toddler but we just moved a couch to block the entry from the livingroom to the front area and that worked well. The home is tiled so it was easy to keep the floors clean. The beds were comfortable and the pillows were mixtures of full and flat to suit all preferences. The home smelled nice and did not have the mild moldy smell many FL homes can have from the high humidity in the area. The owners were a pleasure to work with, very accommodating, helpful and prompt to answer my silly questions about where items in the house were and how to work locks etc We will for sure stay here the next time we visit orlando area. This villa felt like home and was hard to leave. It truly is so comfortable and I am a hard one to please! If you are reading this and considering this home...seriously do not continue your search. There is so much that can go wrong when renting homes on vacations. But this one does everything right!

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Price per night from

$212

Poolsidevilla Glenbrook Rolling Green Dr CLERMONT

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Relaxing Stay with family in condo” we had a relaxing stay at the condo mainly the kids had good time in the heated pool and game room. Condo had all the amenities exactly stated in the ad and looked same as in the pictures. It is closer to the Disney World parks. It had walmart and other shopping area within few miles.It was easy check-in and check-out and well managed.Looking forward to stay again sometime this year.

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Price per night from

$160

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