Vacation Rentals & Villas in Old Town

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102 Houses

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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Price per night from

$115

Disney World 2 Miles

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$136

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

RVH_049R Cabana Court Villa

Reunion house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$189

Disney Vacation Rental, Private Townhouse in gated community

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$163

Sweet Escape

Windsor Hills townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$166

⭐Great Value Villa w/ Private Pool - Nearby Disney Resort⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$265

5 bed beauty with beautiful peaceful lake view!!

Intercession City house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 5 minutes

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Price per night from

$217

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$304

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Price per night from

$117

**2BR/2Bath Condo Near Disney–gated resort, free Wifi & parking

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$115

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Price per night from

$164

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$401

Storytellers Villa

Four Corners villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Truly Amazing” Storytellers the most amazing place to stay. I will definitely return. The owner was always prompt on responding to emails and went above and beyond helping us with our stay. My family and I enjoyed the pool, the cinema, and spa during our stay. We had absolutely no problems with our stay at Storytellers. My 5 year old granddaughter loved the Frozen Room and didn't want to come home. The house is so inviting and beautiful. This house is a must if you are planning a trip to Kissimmee area.

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Price per night from

$395

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

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$344

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.

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Price per night from

$408

Windsor Hills 5BR/ 5BA SF Pool Villa,3MI to disney

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$247

“Very welcoming and worth it !” Me and my family absolutely loved this vacation house everything was so welcoming and near perfect ! This house is definitely something we will never forget and hopefully when we come back we will be able to rent from kim molnar again ! Everything was to a T ! Thank you so much kim !

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Price per night from

$458

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Price per night from

$171

The Fountains (Bluegreen)

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$258

5 Star Family Home with Water Park, Private Pool, Hot Tub 2 Stoplights to Disney

Four Corners house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

“Perfect for everyone's needs and in an excellent location!” From long before we arrived we knew how excellent a villa this was, as the owner and the management team were so incredibly helpful and willing. Including the management team assisting me with purchases to go in the home before I arrived and Susan the owner answering all my crazy questions! In fact I'm going to miss our email chats! On arrival in the home we found everything perfectly clean tidy and in order with an excellent welcome pack to see us through before our big shop. Being a mum of young children I was delighted with the huuuge washing machine and dryer. We need these in the UK. The children loved the pool and the games room and spent lots of happy times there, as did the adults after the kids had gone to bed. We unusually chose not to hire a car and we got around no problem. Disney, particularly animal Kingdom is only a short distance away and universal is only about 25-30 mins. I prebooked a lot of journeys with a company called happy limo who were absolutely outstanding in their punctuality and ease of booking. Anyway back to the house, every bedroom was perfectly appointed with all you could need. The living areas were very spacious even with 7 adults and 2 children. We never once felt on top of each other. The shop and communal pool at Windsor hills is a nice short stroll away and Windsor Hills itself is very clean, well laid out and very secure indeed. I could not recommend this house highly enough and am very pleased I chose this one. I spent weeks and weeks searching villa rentals before settling on this house so I learnt a lot about the different features and prices of villas and I do feel that this one fitted the bill perfectly.

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Price per night from

$315

MINUTES TO WALT DISNEY WORLD'S FRONT GATE

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$160

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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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!

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Price per night from

$265

Windsor Hill Resort (near Disney) YaYa's Place - 3 Bedroom 2 Bath 1st Flr Condo

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great location to everything in Orlando and Disney!” Wonderful Three Bedroom Unit. Had all the amenities one could want and more. We loved our time at Ya Ya's place. Clean and close to everything.

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Price per night from

$189

Marriott's Cypress Harbor Resort

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$180

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

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Price per night from

$177

Wyndham Bonnet Creek Resort

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Wonderful Stay!” We had a wonderful Christmas break at Wyndham Bonnet Creek. This was the best vacation rental ever! The resort is beautiful, quiet but close to everything, WDW theme parks, restaurants, shopping centers, etc. It has all the amenities you would expect. Kids loved the pools and hot tubs. The condo was very clean and spacious, with a full kitchen and a big dining table. We all enjoyed our stay. Highly recommended! Randy (the owner) was very responsive to our inquiry and questions and had everything set up for us before we arrived. Thanks!

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Price per night from

$245

♥EEV♥ Immaculate Family Home - Sunny Private Pool & Spa - Gated Resort

Loughman villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$114

RVH_171R Whisper Way's Finest

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$197

Pooh's Palace in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$516

Spacious condo | extra amenities | epic lake-view

Orlando apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Everything we could have wished for and more!!” Just back from a two week stay here. Condo looks exactly as it does in the photos, stunning! We have been to Orlando many times, however this is by far the best condo we have ever stayed in. Everything went really smoothly, from booking, paying and getting all the necessary information required. The location is excellent, close to parks and the pool was great also. We had decided to take it "easy" this time round in Orlando and having such a beautiful place to stay in was wonderful. Great to sit outside on the porch in the evening watching various fireworks and enjoying the evening sun. The condo was also well equipped and felt really at home here. Would recommend and hopefully will return soon.

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Price per night from

$196

sheraton vistana resort

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$295

September Fall Fun in the Sun Mickeys Place - Wiltshire Villa

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$212

Disney Dream: Hot Tub, Pool, Xbox, Games Room, Clubhouse, 15 min to Disney

Intercession City villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$343

Unit 26- 4 Bedroom Emerald Island 2711

Kissimmee townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 7 minutes

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Price per night from

$125

8br/6ba pool villa from $280/nt , Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$344

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rentals in Old Town

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