Vacation Rentals & Villas in Winter Park

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259 villas

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

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sauna

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Price per night from

$252

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.

Match: Sauna

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Price per night from

$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

Match: Sauna

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$144

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

ChampionsGate house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Sauna

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Price per night from

$137

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.

Match: Sauna

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Price per night from

$110

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

Match: Sauna

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Price per night from

$344

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.

Match: Sauna

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Price per night from

$217

Amazing Disney Oasis Condo with Sauna and Gym

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Sauna

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Price per night from

$125

Luxury 3 Bedroom Lock-Off Condo in Orlando

Orlando private room

  • 1 bedroom
  • 3 bathrooms
  • sleeps 12

Match: Sauna

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Price per night from

$213

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$287

From $100/NT,1.5 Mile to Disney ,1808 sq ft 4br/3ba townhome with lake view

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location” We had great times in Oakwater, all was perfect! The house is fully equipped, all is clean, new and works perfect!It is an ideal location, close to everything. Near the home are so many great restaurants such as: Bonefish, Longhorn, Golden Corral, Ihop, Bahama Breeze, Buffalo Wild Wings, Flippers Pizza*, Red Lobster and lots more! The super target is within 2 min as well as the Publix.It is also located in very quiet area. There are great sports facilities, tennis court, and the pool area itself is fantastic. We enjoyed it very much and the pool s huge and warm !!! We loved it and will definitely recommend to our friends and family!

Responds fast! avg. 1 hour 27 minutes

Match: Sauna

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Price per night from

$121

The Ever After Estate - 13BR Sleeps 45 People & Has 62 Private Acres

Clermont house

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 43

“Everything you could ever imagine !!!” My new Wife and I just got back from our stay. We held our Wedding there. We had both our immediate families stay with us during 3 days of our 4 day stay. Plenty of room for all, we had 15 adults and 8 kids total. This place is just so amazing. My wife and I toured it prior to our stay and missed so many things because there is so much detail. Our favorite place was the pool area. The day after our wedding some of us hung out at the pool for a couple of hours. The kids all had a blast between the pool slide, video games, ball pit, mini golf, and movie room. This made it easy for us to focus on set up and tear down for the wedding. We had 220 guest during our day and everyone loved the place. Biggest question was how did you find this place. Great photos from our day hit facebook immediately with babies on the Carousels,kids playing mini golf, and people around the tropical pool setting. Andrew, Felicia, and his staff were very helpful. Andrew answered all our questions with fast response times through out the planning. Felicia was there when we checked in and ensured we were settled and answered any last minute questions. The detail andrew put into his Estate is amazing. Every thing out there takes you away from your everyday. We are so lucky that such an awesome place was shared with our family and friends to enjoy. It was the perfect place to hold our special day. The last day I spent an hour taking photos of the Estate in which I noticed the incredible landscape,a touch that just simply takes your breath away on the beauty of life. Andrew thought of it all. The only down fall, which was our fault, is that we did not have enough time to enjoy everything. This was due to a short stay, wedding set up and tear down. Our next stay will be longer. My older Sister from Philly was talking about a family meet up next year. Boy I Hope so. All our Wedding dreams came true. Thank you Ever after Estate and Thank you andrew.

Match: Sauna

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Price per night from

$1,985

Awesome Mickey Themed Kids Rooms-bbq in back yard!

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sauna

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Price per night from

$137

9br/6ba pool villa from $380/nt,Close to Disney

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 20

“Nice house for large family” The house itself is very attractive. The bedrooms were very well appointed. There were sufficient towels and plates, silverware, glassware, etc., for our party. Our major problem was the parking. It is a very over-crowded community and we had five cars (to be expected in a six master-bedroom house that fits 18+), and we often had trouble parking near the house. My only other complaint (if you could call it that) was the trash. We had one large trash can and it got picked up on Monday morning. We were there for six full days with 13 people, so we easily refilled it up and then had multiple loose bags with nowhere to put them through the end of our stay. No recyclable can was available, either, so recyclables had to go in trash bags. Owner was easy to work with. Thanks for a very nice home!

Responds fast! avg. 1 hour 27 minutes

Match: Sauna

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Price per night from

$401

The Sweet Escape - 11 Bedrooms on 5 Acres! Sleeps 52 Guests!

Clermont villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 50

Match: Sauna

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Price per night from

$1,295

Upgraded 5-star Penthouse, Bahama Bay near Disney

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Very comfortable stay - enjoyed every moment of it!” Very spacious accommodations. We stayed 2 families with little girls who were very anxious to see Disney World parks. The condo was perfect for our stay, we were just about 20 minutes from Magic Kingdom so we were there in a snap. The resort is beautiful and we can't wait to come back again. There are multiple swimming pools, one close to condo's building, another one - bigger and open until 10 pm - near the club house / reception. Another similar size pool at the restaurant area with little white sand beach, volleyball net and table tennis. Also we enjoyed playing tennis on the real hard court surface near reception, very good quality and with lighting. When you need a day off from visiting parks and all these crowds staying on the resort is the great option. Shopping is very close to the resort - 7 minutes drive to Walmart, so you could get anything you need, open 24 hours. We also recommend buying tickets to all attractions at the Walmart since there is a small discount vs buying at the gates. Overall - great experience, highly recommend to anyone. Will definitely come back again!

Match: Sauna

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Price per night from

$227

❤️ Super Cozy Home Minutes to Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Birthday Trip!” I do believe this might have been the funnest trip I've ever taken in my life. Having every single thing just minutes away from you was such a delight and such a pleasure to not have to drive around constantly in the car. This community is gated and seems like a really fun place to actually buy a vacation home. Actually, while we were there we looked into it and might be doing the same thing that this particular person is offering on TripAdvisor as well! First of all, the house was just absolutely amazing... Bigger than my own home even. It was just me, my son and my husband and our house was absolutely humongous. We actually had thought we would have another family with us but it fell through. Everything was clean and perfect. There were many things like dishwasher, laptop, printer, hair dryer, straightener, toiletries, food! When we arrived, we already had some basic needs that were furnished To Us by the owners. It was such a treat to see that they really cared about us to furnish those things! There was a perfect screened in porch out the back over looking a little bit of a water marsh where we got to watch the birds everyday. The wildlife in our particular yard was extremely delightful. From frogs to lizards two birds two cranes we had an amazing time when we were relaxing at home. To my delight, there were also three swimming pools in the complex. One of the pools were in the middle of the community which was right down the street from our home, then there were two others inside the clubhouse which were also fantastic. We really enjoyed the hot tub and sitting underneath the shelter when it started to rain. Since I knew it would be very hot and we would be extremely exhausted, I asked for a maid service halfway through our vacation and I'm so happy I did. It was nice to come home after dinner to a 100% clean house with clean towels and everything perfect. I recommend that you get the service as the cleaning lady does an excellent job! The next time we booked our Walt Disney World vacation I will be using this home again without a doubt. Even though we stayed 7 days, we still did not get to see everything that we wanted to. Next time we come down we are doing 10 to 12 days for sure and cannot wait to come back to Vista Del Lago. I was really surprised on how many friends we made while we were there!! If you are looking for a family home that could easily sleep 7 people, please do yourself a favor and book this, you will be so glad that you did!!

Match: Sauna

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Price per night from

$252

4 Bedroom Villa 2 Miles from Disney Entrance

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sauna

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Price per night from

$138

The Great Titan

Orlando villa

  • 14 bedrooms
  • 16 bathrooms
  • sleeps 30

Responds fast! avg. 2 hours 21 minutes

Match: Sauna

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Price per night from

$4,008

Lovely Family Executive Townhouse at Regal Palms Resort

Davenport townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Sauna

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Price per night from

$155

Match: Sauna

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Price per night from

$164

5 BED LUXURIOUS VILLA CLOSE TO DISNEY GATED COMMUNITY

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Sauna

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Price per night from

$207

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sauna

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Price per night from

$401

WESTGATE LAKES RESORT & SPA-Orlando Florida

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 55 minutes

Match: Sauna

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Price per night from

$217

Affordable and Comfortable Orlando / Disney 3 Bedroom Home

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sauna

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Price per night from

$148

New Luxury Villa Europa with Pool Theater /10 min to Disney

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sauna

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Price per night from

$344

WESTGATE LAKES RESORT & SPA-Orlando Studio

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 55 minutes

Match: Sauna

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Price per night from

$129

Westgate Lakes, Orlando Florida - 4 Bedroom Villa - Huge Resort with everything

Orlando hotel apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

“Worth It!!!” Our family stayed at Westgate Lakes for one week during Spring Break. We had a four bedroom condo and the space was fabulous!!! We were more than impressed with the resort staff and all the ammenities. The location was also very excellent and so easy to find and so close to the attractions we wanted to visited. The resort was very clean in all areas and very safe and secure for our family.

Match: Sauna

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Price per night from

$408

The Fabulous SKC Villa

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sauna

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Price per night from

$172

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sauna

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Price per night from

$295

LUXURY DREAMS DISNEY HOUSE PRIVATE POOL SPA GAMEROOM

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Sauna

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Price per night from

$400

Match: Sauna

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Price per night from

$171

Match: Sauna

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$257

8960 Paradise Palms, Superb 4 Bedroom House with a Pool and Sauna

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 minutes

Match: Sauna

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Price per night from

$109

2BR townhome - Resort waterpark! 10 min to Disney

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 16 minutes

Match: Sauna

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Price per night from

$207

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sauna

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Price per night from

$287

⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

“Fantastic Stay” The home was in a beautiful community and there was a huge resort pool with all the things one would look for in a resort setting. The home itself was immaculate and very clean upon arrival. The beds were all comfortable and the rooms were spacious. We enjoyed the home and the resort so much that we actually spent a few days less at the parks. The reservation process was simple and straightforward. All in all a great vacation!

Match: Sauna

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Price per night from

$265

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sauna

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Price per night from

$180

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