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Kissimmee Apartments & Vacation Rentals - 3888 Rentals Available

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3,888 Vacation rentals

(61)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great big house Excellent location for parks Very reasonable Owner gave great directions for when you show up Also pool really came in handy”
- Review left on 06/28/2018

$144.00

Excellent (61 reviews)

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from $144.00 / night

(53)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The accommodations were excellent, all the amenities required for a comfortable stay, the place was very clean, the HVAC worked fine no issues. I recommend staying here to anyone. Than you for everything Manny and Carmen we will be back soon...”
- Review left on 01/23/2017

$89.00

Very Good (53 reviews)

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from $89.00 / night

(6)

1 / 27

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

$85.00

Average (6 reviews)

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from $85.00 / night

(23)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The location is perfect for a Disney vacation. You can't get much closer to DisneyWorld without staying onsite. I prefer to stay offsite whenever we visit, because it's nice to be able to "escape" from all the Disney magic every now and then. The...”
- Review left on 10/27/2017

$89.00

Excellent (23 reviews)

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from $89.00 / night

(9)

1 / 33

Kissimmee House

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

“We've stayed in a lot of vacation homes in this area over the last 20 years and I have to say that this was one of the best equipped that we've ever stayed in. The house has been recently renovated and everything was very nice and clean. The pool is...”
- Review left on 03/11/2017

$189.00

Excellent (9 reviews)

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from $189.00 / night

(18)

1 / 17

Kissimmee Apartment

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 11 minutes

$79.00

Excellent (18 reviews)

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from $79.00 / night

(5)

1 / 14

Kissimmee Villa

  • 3
  • 8
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 43 minutes

“The house was clean and very nice. The pool was so clean. The house has air conditioner, satellite dish 2 TVs. It was great .. And I will definitely stay in it next time I visit Orlando...”
- Review left on 08/24/2016

$89.00

Very Good (5 reviews)

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from $89.00 / night

(3)

1 / 23

Kissimmee Apartment

  • 3
  • 8
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 28 minutes

$80.00

Excellent (3 reviews)

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from $80.00 / night

1 / 9

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$287.00

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from $287.00 / night

1 / 38

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 52 minutes

$147.00

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from $147.00 / night

(4)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 46 minutes

“We had a wonderful time at this home. The house is spotless and the bedrooms are all very comfortable. The pool is lovely and we also took advantage of having access to the huge clubhouse pool . The commute to Disney was easy and quick. The owner...”
- Review left on 05/16/2016

$195.00

Very Good (4 reviews)

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from $195.00 / night

(13)

1 / 43

Kissimmee House

  • 8
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 45 minutes

“This vacation home is absolutely beautiful! It looks identical to the pictures on the website. We stayed at the Reunion Emperor in March 2017 for a total of 8 nights. Our group consisted of 6 adults and 7 children - three families all under one...”
- Review left on 01/20/2018

$342.00

Excellent (13 reviews)

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from $342.00 / night

(57)

1 / 64

Kissimmee House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“My grandson was invited to Select 30 at ESPN. Graham told me this house was only 15 minutes away. This house is a perfect location for Disney facilities. Once out of the subdivision, you make one turn and you are at Disney. We enjoyed the pool at...”
- Review left on 08/31/2017

$131.00

Excellent (57 reviews)

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from $131.00 / night

(2)

1 / 23

Kissimmee Villa

  • 4
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 11 minutes

“From the time we viewed this beautiful home on the website, we knew this was the place we wanted to celebrate our 2nd. Anniversary here. This place is decorated with a touch of sophistication and elegance yet it made you feel at home once you walked...”
- Review left on 10/07/2015

$109.00

Very Good (2 reviews)

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from $109.00 / night

(1)

1 / 61

Kissimmee Villa

  • 7
  • 14
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“Location, location, location! This well- equipped neat, spacious and cozy luxury home is close to everything you'd ever want to do in Orlando,Florida. Children open the patio doors and they are in their own pool, while the family relax in or out of...”
- Review left on 03/22/2016

$131.00

Excellent (1 reviews)

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from $131.00 / night

(28)

1 / 20

Kissimmee Villa

  • 3
  • 8
  • min stay varies
  • Nearest beach 104 mi
  • Swimming pool
  • Child friendly
“Was in a great Location close to dining, shopping and attractions. A little further from the beach then expected, but the neighborhood was quite and the house was bigger than expected. A perfect house for a family to stay in...”
- Review left on 09/26/2016

$104.00

Very Good (28 reviews)

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from $104.00 / night

(43)

1 / 36

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Great location. Near Disney and shops. The owner were very nice ? called to see if everything is o.k, and agreed to a late departure. The view of the lake is wonderful and the pool is great. The kids rooms upstairs was the one thing I liked less....”
- Review left on 10/17/2018

$150.00

Excellent (43 reviews)

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from $150.00 / night

(4)

1 / 41

Kissimmee Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 2 minutes

$102.00

Very Good (4 reviews)

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from $102.00 / night

(8)

Certificate of Excellence

1 / 33

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

“All around great stay. Bob and Diane were extremely helpful. Would highly recommend them for your vacation needs...”
- Review left on 07/29/2018

$86.00

Excellent (8 reviews)

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from $86.00 / night

(4)

1 / 66

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“The location is great. Close to all the parks. Restaurants and grocery right up the street. The house was fabulous. We had 14 people stay in the house, plenty of room. The pool and hot tub were used every night...”
- Review left on 11/25/2014

$137.00

Excellent (4 reviews)

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from $137.00 / night

(14)

1 / 40

Kissimmee Apartment

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 46 minutes

“Great value for your money. The condo was very clean. I was really impressed with the unit. There was plenty of space for everyone to spread out and enjoy themselves. It was well stocked with linen. The washer and dryer worked great. Unit has a...”
- Review left on 04/30/2015

$98.00

Very Good (14 reviews)

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from $98.00 / night

(43)

1 / 57

Kissimmee House

  • 6
  • 12
  • 4 nights min
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 19 minutes

$218.00

Excellent (43 reviews)

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from $218.00 / night

(17)

1 / 38

Kissimmee Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 24 minutes

$109.00

Excellent (17 reviews)

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from $109.00 / night

1 / 86

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 113 mi
  • Swimming pool

Responds fast! Avg. 1 hour 24 minutes

$172.00

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from $172.00 / night

(20)

1 / 16

Kissimmee Villa

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The property itself was very nice with a few small problems. We had to purchase an HDMI cable in order to view the TV in the family room which we left on the set. The lamp in the family room was damaged by a previous renter and inoperable. Upstairs...”
- Review left on 04/15/2018

$143.00

Excellent (20 reviews)

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from $143.00 / night

(3)

1 / 118

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 3 minutes

$81.00

Very Good (3 reviews)

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from $81.00 / night

(15)

Certificate of Excellence

1 / 38

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 21 minutes

Certificate of Excellence

“This house is everything the ad states and more!! The location is perfect and is so conveniently located to Disney, fantastic mini putts, a beautiful golf course, and restaurants. The lay out of the house is fantastic allowing everyone in your party...”
- Review left on 03/05/2018

$172.00

Excellent (15 reviews)

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from $172.00 / night

(9)

1 / 47

Kissimmee House

  • 4
  • 8
  • 4 nights min
  • Nearest beach 122 mi
  • Swimming pool
  • Child friendly
“We really enjoyed this home. It was a nice break from the busyness of the Disney parks. We loved having an entire house to relax in rather than a hotel room, especially since we are a family of 6. The pool was nice as well, we loved having it all...”
- Review left on 11/30/2016

$149.00

Very Good (9 reviews)

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from $149.00 / night

(2)

1 / 18

Kissimmee House

  • 8
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$228.00

Excellent (2 reviews)

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from $228.00 / night

(8)

1 / 23

Kissimmee Villa

  • 8
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“this is a very nice home for big families and is very short drive to Disney world would stay there again”
- Review left on 12/05/2016

$228.00

Very Good (8 reviews)

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from $228.00 / night

(11)

1 / 33

Kissimmee Townhouse

  • 3
  • 7
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“Will recommended to friends when they are planning to go Orlando in July/August.Closed to Disney world, shopping centres, etc...”
- Review left on 04/18/2016

$63.00

Excellent (11 reviews)

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from $63.00 / night

(71)

1 / 23

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 35 minutes

“My Wife and I and Her Brother and his wife ( we are all in our mid sixties) stayed in this rental for the month of February. When we arrived everything was set up well for us from clean linens to the dining room table all set for a meal. The...”
- Review left on 03/08/2017

$68.00

Very Good (71 reviews)

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from $68.00 / night

(30)

1 / 19

Kissimmee House

  • 4
  • 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 24 minutes

“We had a last minute vacation opportunity and Sheryl was so accommodating and excellent and we loved her place! We had 5 kids and 2 adults and there was tons of space to relax and have private space. The pool was amazing!! It was the perfect temp and...”
- Review left on 07/07/2018

$137.00

Very Good (30 reviews)

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from $137.00 / night

(6)

1 / 28

Kissimmee Townhouse

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
“Oakwater was very clean. The pictures were true. My family and I stayed for two weeks. We would definitely stay here again in the future...”
- Review left on 08/28/2017

$109.00

Very Good (6 reviews)

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from $109.00 / night

(12)

1 / 26

Kissimmee House

  • 7
  • 16
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Our stay was just breathtaking. The best stay ever! For most of us it was our first time experiencing a Vacation home and they definitely suggest to come back again! Everything was in place , everything was clean and well taken care of, the pool was...”
- Review left on 09/12/2017

$172.00

Very Good (12 reviews)

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from $172.00 / night

(4)

1 / 22

Kissimmee House

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house is extremely comfortable and accommodating. We had 6 adults and 3 children and there was plenty of room. The home is very clean overall and had lots of the essentials. For anything extra you may need there are tons of local shopping...”
- Review left on 11/17/2017

$172.00

Excellent (4 reviews)

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from $172.00 / night

(1)

1 / 25

Kissimmee House

  • 6
  • 12
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The house was beautiful. It was clean when we arrived and in very good condition. Everyone enjoyed the playroom. The house is very spacious. I would love to visit this house again when I come back to the area. Would love to see a larger television...”
- Review left on 12/04/2013

$183.00

Very Good (1 reviews)

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from $183.00 / night

(24)

Certificate of Excellence

1 / 64

Kissimmee Villa

  • 4
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 5 minutes

Certificate of Excellence

“My wife and I had an enjoyable, relaxing 8 week stay at the villa this past winter and were impressed with the cleanliness while the neighborhood itself is quiet and serene. We were close to a local park with basketball and tennis courts along with...”
- Review left on 03/28/2016

$126.00

Excellent (24 reviews)

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from $126.00 / night

(9)

Certificate of Excellence

1 / 29

Kissimmee Villa

  • 6
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 120 mi
  • Swimming pool

Responds fast! Avg. 54 minutes

Certificate of Excellence

“We went with two families and everyone loved the place! It was close to Disney. Relaxing in the hot tub after a day a Disney was perfect...”
- Review left on 12/23/2017

$229.00

Excellent (9 reviews)

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from $229.00 / night

(14)

Certificate of Excellence

1 / 12

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

“The property is perfect. The pictures don't do the pool justice. It is one of the nicest pools you'll see on a vacation property. We had 3 children all 3 and under and it was no problem at all. The drive to Disney was a very quick and easy drive and...”
- Review left on 12/02/2017

$92.00

Excellent (14 reviews)

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from $92.00 / night

About Kissimmee

Whether you want to visit theme parks or nature preserves, Kissimmee is the place to be in Central Florida. Take your pick from dozens of luxurious Kissimmee villas, and enjoy a dip in the pool and plenty of fun in the Florida sun.

Introduction to Kissimmee

Located just a short hop away from Orlando, Kissimmee is a small city that offers quick and convenient access to a whole range of family friendly activities. When you want to take the kids on a trip to Central Florida but don’t want the stress or expense of vacationing at the theme parks, consider staying at one of the affordable Kissimmee villas. Vacation properties in Kissimmee give you the space to have a good time without breaking the bank.

Kissimmee Climate

Like most of Central Florida, Kissimmee enjoys hot, humid summers followed by mild winters. If you visit in December or January, you’ll find temperatures around 60 degrees, while temperatures top out around 90 in July and August.

How to Get Around Kissimmee

If you’re flying to Kissimmee, Orlando International Airport is an easy 25-minute drive away. Public busses and private shuttles can transport visitors around the Kissimmee area, but if you want to explore on your own, renting a car is your best bet. You can easily get from your vacation home to the theme parks, or to the natural attractions, on your own schedule with a car.

Visit the Parks

The rides and attractions at Disney World are just a short drive away, but Kissimmee also boasts several of its own parks. Right on Lake Tohopekaliga, Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for family get togethers, and fishing piers for everyone. If you time your visit right, you can even catch one of the many festivals or events on the park’s outdoor stage.

If you’re looking for something more outdoorsy, visit Shingle Creek Regional Park, which encompasses over 1,000 acres. Canoe along the creek, hike the trails, and enjoy a picnic near the park’s historic pioneer homes. Even more impressive is the Disney Wilderness Preserve, which includes 11,500 acres and over 1,000 plant and animal species. Explore wetlands, swamps, and a freshwater marsh while spotting bats, snakes, and even panthers.

Shop and Dine in Old Town

When you’re ready to do some shopping or grab a bite to eat, head straight for Kissimme’s Old Town neighborhood. Here you’ll find everything from souvenir shops to places to stock up on warm weather gear. To fuel up for more adventures, dig into pizza, Tex-Mex, or pub grub. You can even enjoy a night out at one of the live music venues or nightclubs in Old Town.

Just a few miles from Disney, Kissimmee offers the best of everything. With parks and preserves that will keep everyone entertained, Kissimmee villas that comfortably fit the whole family, and easy access to all the fun at Disney World, Kissimmee is a great vacation destination.


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Kissimmee, Florida Travel Tips

Families looking for vacation rentals in Kissimmee, FL have many accommodations to choose from, but renting a home is the best bang for your buck while on a Kissimmee vacation. Rentals by owner offer much more space and privacy than a hotel room, and ensures that homes are very well maintained and updated. Keep reading to learn more tips about how to have a memorable vacation in Kissimmee.

Beaches and Parks

St. Cloud Lakefront Park and Beach offers a fishing pier, splash pad, family picnic area, volleyball court, and playground. Located along the breathtaking Lake Tohopekaliga, this park is a great place to spend a relaxing afternoon.
Cocoa Beach, located just an hour's drive from Kissimmee, features beautiful weather, whale watching, fine dining, and golf.

Theme Parks

What probably comes to mind when looking for houses for rent in Kissimmee, FL is the town's close proximity to world-famous theme parks. The magic of Disney World, Universal Orlando, and SeaWorld are only a short drive away while staying at this delightful vacation spot.
Walt Disney World needs no introduction. As the most visited entertainment complex in the world, this beloved attraction boasts four theme parks and two water parks.
Universal Orlando consists of Universal Studios, Islands of Adventure, and Wet N' Wild Orlando. Visitors can enjoy a variety of shows, dining, and events right within the borders of the park.
SeaWorld is another favorite of those visiting the Orlando area. With tons of shows, exhibits, dining, and shopping, there is surely to be something for everyone to enjoy. Kids will adore seeing killer whales, dolphins, manatees, sharks, polar bears, flamingoes, and penguins up close.

Outdoor Adventures

Golf is a popular sport in Florida because of its year-round sunny weather. If you're a seasoned pro looking for challenging courses or just want to play mini-golf with the kids, Kissimmee has you covered.
Hot Air Balloon Rides are a great way to top off your Kissimmee vacation. Take a sunrise balloon ride over Central Florida's beautiful landscape and check out the wildlife from high above.

Fun With Kids

The kids will have no shortage of things to do while enjoying their time in Kissimmee. Kids and parents will have a blast exploring the nearby attractions. In addition to the great outdoors and amazing theme parks, the Kissimmee area also features lots of relaxing, family-friendly activities.
Medieval Times Dinner & Tournament is guaranteed to always be a fun time. Have dinner while being entertained by a live-action jousting tournament.
Osceola County Pioneer Village and Museum features many exhibits depicting life in the 19th century. Located in northwestern Osceola County, the Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
Green Meadows Petting Farm , located just minutes from Orlando, teaches kids about a variety of farm animals and even allows them to milk a cow. The farm also has a train ride and offers pony rides.
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