Vacation Rentals & Villas in Old Town

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656 Houses

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

Match: Private outdoor pool (heated)

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Price per night from

$123

Spacious 4-bed lakeside pool villa near Disney

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great Location” We stayed from Saturday to Saturday. Overall the house was good. Pros: Clean, spacious, close to Disney Parks, close to stores, very quite place, easy access, comfortable furnitures, Cons: master bedroom was hot, internet service went down mostly at night time like it has a timer at night, and odd times during day time only for few minutes, the pool only the first day when we arrived pool was with cloudy water and water very hot all the time, we think the heater was on. Cable TV, we had two afternoons that we had no signal. The house has two blenders both not working. No raw meat knife, we had to buy our own for cooking. We wanted to use the garage to place our car, it has many objects we could not use it.

Responds fast! avg. 1 hour 57 minutes

Match: Private outdoor pool (heated)

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Price per night from

$162

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

Match: Private outdoor pool (heated)

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Price per night from

$121

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

Match: Private outdoor pool (heated)

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Price per night from

$161

3 bedroom home private pool near Disney I4 & shops

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Supervisor” It was really nice. We stayed for three nights and we enjoyed it. It was close to the parks, to publix, restaurants, and gas stations. Only one negative was that there were no phone signal.

Responds fast! avg. 44 minutes

Match: Private outdoor pool (heated)

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Price per night from

$121

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Price per night from

$271

Beautiful 6 Bedroom Home in Reunion Resort and Spa

Reunion house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

Responds fast! avg. 14 minutes

Match: Private outdoor pool (heated)

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Price per night from

$487

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 19 minutes

Match: Private outdoor pool (heated)

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Price per night from

$344

“A Magical Stay” What's not to love about this home! First and foremost Brandie herself is a genuine person who really cares about the people who stay at her home. From the initial contact of a personal phone call, to her follow ups on every little question, to her wishing us a safe trip to a thank you and welcome home at the end, Brandie is truly a great family person! The home itself was as described in other reviews and more. The location to the clubhouse could not have been better. A short walk down the path (100yds maybe) and the kids were relaxing by the lagoon pool! The added security of a gated community provided additional piece of mind even though you are only 5mins from Disney. The staff at the community became like family before we left. Friendly, cheerful, always willing to stop and talk about anything and everything! The home itself is exactly as pictured! Clean and comfortable made for it enjoyable to return home for afternoon breaks from the park. The Disney bedroom was the room of choice for our youngest! The downstairs bedroom provided a nice separation for our oldest to have her space when exhaustion took over:). We have rented homes before when traveling to Disney and Brandie's is at the top of the list! From location, ease of access, amenities, cleanliness, comfort and exceptional (what I will call) customer service and value, you won't find a better place to stay or person to work with then Brandie and her home!!! We will definitely be back again!!! Thanks Brandie :)

Match: Private outdoor pool (heated)

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Price per night from

$228

RVH_268ER Golden Sunset Villa

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$363

4/3 Private Lakefront Town Home at Storey Lake Resort-Near Disney Theme Parks

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$206

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!

Match: Private outdoor pool (heated)

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Price per night from

$212

“Disney vacation” Beautiful vacation home! We loved the spacious living arrangement and proximity to a shopping center. Only about 15-20 minutes to Disney parks. Would certainly recommend this house and stay again!

Responds fast! avg. 30 minutes

Match: Private outdoor pool (heated)

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Price per night from

$170

Reserve at Town Center Lake View Disney Villa with free Wi-Fi and Netflix

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 7 minutes

Match: Private outdoor pool (heated)

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Price per night from

$132

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Price per night from

$115

Reunion| Golf Course Community | 5 Star Resort 873

Reunion house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$249

Sweet Escape

Windsor Hills townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (heated)

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Price per night from

$166

Villa Journey - 3 miles from Disney, 2 Masters and a Private Pool & Spa!

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great property for the whole family.” It was a great property for the family and a very good location. But because of the cold weather during our stay we could only use the pool and spa one day, and in this time of the year the sun is only in one corner of the pool area.

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$195

Large Sunny Pool Home Near Disney and Golf

Orlando villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

“Very Good” Nice quite location. It is close to the theme parks and all the family attractions. My family is well pleased with the spacious home, The children and adults are taking full advantage of the pool throughout the entire day prior to leaving the house and upon our return.

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$182

Solterra Resort | Disney Area | 5★ Community 4225

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

“Wow!!!!” What an amazing home, it has the Wow factor from the second you open the door, equipped with everything you need , providing all home comforts and more. Pool and spa are perfect and with pool heat we could enjoy this luxury anytime from early morning to evening and exactly what was needed after a tiring day at one of the parks..I would highly recommend this villa and will Most certainly be back with the family ....

Match: Private outdoor pool (heated)

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Price per night from

$121

4776JW VILLA 6 BED/5 BA (SANITIZED)

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 3 minutes

Match: Private outdoor pool (heated)

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Price per night from

$211

CONSERVATION - HOT TUB - FREE POOL HEAT - Tax Inc

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect Florida Holiday” A thoroughly enjoyable 4 week stay in a property that was equipped with everything you could possibly want to make it a home from home. As described this was an extremely well presented home in a very good location that made it easy to access all the major attractions, golf courses and shopping centres. We made regular use of the golf clubs and as the house backs onto the nearby conservation area of Shingle Creek we explored it many times on the bicycles provided with the home. We enjoyed the pool and hot tub which benefited from a covered lanai and privacy fencing and the free pool heat was much appreciated. Overall the property was first class and excellent value for money and we will certainly be returning.

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Price per night from

$241

Paradise Found Kissimee Rental

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Lovely Get-away” We were very pleased with this house. The split floor plan was a nice plus and my husband and I loved the master suite with our own bathroom and walk-in closet. The kitchen was large and fully equipped. We liked the smaller table in the kitchen which is where we played cards and games. It was also nice to have a large dining table so our whole group could eat together. The setting is beautiful, having the lake view out the back. This was a wonderful home base for our family while in Florida for our son’s wedding!

Match: Private outdoor pool (heated)

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Price per night from

$189

LAKESIDE HAVEN, Windward Cay, The "hidden jewel" of Kissimmee

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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$207

Beautiful and Spacious Orlando Pool Home

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Awesome Place to Stay!” Stayed there for a week and had an absolute ball. Villa is extremely clean and exactly as pictured on the website. We had so much fun in the pool we forgot the Villa had a pool table! Definitely booking this one again next vacation!

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$138

Solterra | 5★ Clubhouse | South Facing Home 5423

Davenport villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

“Thanksgiving Holiday” We had a wonderful stay! The house exceeded our expectations! Very spacious, well equipped with plenty of towels and linens. We would definitely go back!

Match: Private outdoor pool (heated)

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$181

Willow View Villa 5+ Bed, 3xKing Master 2xTwin + Den

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Willow View Villa” First, let me say the home is not what you see in the pics. The home has flat screen throughout. The home was convenient to parks, outlets and restaurants. My family and I stay in Davenport a few times a year but this was a last minute trip and based on pics we were really nervous. The home was clean and kids loved the pool. We cooked out and enjoyed the patio. I had 2 problems that was unfortunately fixed the day we were leaving but it was nature not the owner!. The other was the downstairs bedroom smelled like smoke, we sprayed but was in the linen. Again, it was clean but smelled like smoke and being non smokers it was annoying. We spent most of our time on the comfy recliners or at the pool so it was ok. Thank you Martin!

Responds fast! avg. 2 hours 12 minutes

Match: Private outdoor pool (heated)

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Price per night from

$276

Charming 3 Bedroom Home w/ Sun-Kissed Private Pool

Davenport villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$158

RVH_300ER Reunion Retreat

Kissimmee house

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 32

Match: Private outdoor pool (heated)

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Price per night from

$1,740

Disney Pool Home - Pet Friendly

Kissimmee house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 7

“EXCELLENT Property, location and Owner!!” We can highly recommend this Vacation rental property, the location is perfect, very close to the Disney parks, restaurants with varied cuisines, major freeways, etc. The home and pool were EVERYTHING we'd hoped for, it was a very well maintained property, it lacked nothing as everything we required was provided including FREE WiFi! The communication with the owner, Joan, was FIRST CLASS! From the booking thru the rental period and followup afterwards was a very pleasurable experience, we are VERY PLEASED!! We looked at quiet a few PET FRIENDLY properties (we have 3 small dogs) before deciding on this property, mainly due to amenities, location, etc and are pleased to further recommend this property and owner for your vacation property needs! Additionally, we plan on booking this property again if available during out next vacation in the Kissimmee/Orlando area, why look anywhere else?? Our many thanks to the owner Joan and the Property Management for making our stay very memorable!! Thank you Joan!! Mike and Karen Ford

Match: Private outdoor pool (heated)

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Price per night from

$167

“Excellent and convenient choice to visit WDW.” Location was superb, had all conveniences of home. Kids enjoyed the pool after a long day at the park. Wish we could have stayed longer. We will rent here again.

Responds fast! avg. 3 minutes

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Price per night from

$224

Solterra Resort, 5 Star Clubhouse, Lazy River 4095

ChampionsGate house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated)

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Price per night from

$136

Roughtallys Villa

Kissimmee villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

“HOME away from HOME” This property has everything you need for your stay just take your clothes. Property is spacious and well kept. I highly recommend it.

Match: Private outdoor pool (heated)

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Price per night from

$316

Groovy Mouse House with private pool near Disney

Reunion villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated)

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Price per night from

$401

Stunning 4 bedroom pool villa sitting on a lake

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$172

Willowdale Retreat

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$121

Wow Factor-Interior Designers Own 5 bed/5bath Home

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$224

“Budget friendly, spacious home” We loved staying only a few short miles from Disney in a home that could accommodate our large family. Parking was very tight, but we managed. The home offered plenty towels, bedding, dishes, flatware, etc. for our large crew. I was, however, glad I packed some cookware as it would have taken a much longer time to feed a large group with the small cookware provided. I was impressed with how no one had to take cold showers as the hot water heater was able to keep up with everyone taking showers for church on Sunday morning. The air conditioning worked perfectly & the owner had recently purchased a brand new grill. We did have difficulty getting some of the electric outlets to work and one of the overhead lights did not work at all in one of the bedrooms. There were a few issues with ants and roaches when we first arrived, but we purchased bait plus the exterminator came on her regularly monthly visit while we were there & took care of the issue. I guess the biggest inconvenience was that there were no shelves on the refrigerator door. The house would have been perfect had refrigerator had those shelves or there had been a second refrigerator in the garage/game room. It was inconvenient to have to go grocery shopping every 2-3 days because the refrigerator would not hold enough food for a large group. The washer & dryer, however, were huge & plenty big! There were a few other minor issues, but we decided we would rather live with them than have to stay at the house & wait for the management company to come & deal with them. Overall, I would recommend this home to anyone. The owner is obviously trying to keep the house up.

Responds fast! avg. 1 hour 27 minutes

Match: Private outdoor pool (heated)

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Price per night from

$264

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