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Monthly Vacation Rentals Kissimmee Florida

What Are The Popular Points Of Interest Near Where I Can Stay When Travelling To Kissimmee

Solara Resort Kissimmee Florida Clubhouse Tour | Vacation Rental Homes For Sale | $500K

Vrbo Canada offers a large selection of lodging choices near lovely places in Kissimmee. From Vrbo Canada travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Kissimmee Golf Club: 26,790 home rentals
  • Kissimmee Lakefront Park: 22,672 home rentals
  • Medieval Times: 26,396 home rentals
  • 192 Flea Market: 26,764 home rentals
  • Kissimmee Station: 26,264 home rentals

But there are many other points of interest around Kissimmee listed on Vrbo Canada where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

The Epcot International Food & Wine Festival

Book your Kissimmee condo rentals far in advance for the Epcot International Food & Wine Festival. Walk your way around the world and taste different wines and foods from various countries at little popup stalls around the lagoon at this popular fall event.

You could also time your visit to see the Disney World Marathon, held over a weekend every January. Events include a full marathon, fun kids’ runs, and a health expo.

Cheap Vacation Rentals In Kissimmee

4 BR | 3 BA | Sleeps 8 |

  • Private pool

About this property

Water View and Outdoor Spa! Elite Vacation Homes is the preferred Orlando, Disney area home-base among travelers from around the globe. Stay close to just about everything and enjoy easy access to our world-renowned theme parks, exciting golf, mega shopping and exceptional dining.Ideal …

3 BR | 2 BA | Sleeps 6 |

  • Private pool

About this property

Beautiful south facing lakeside villa with electrically heated pool option. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. …

Kissimmee Villa

“Family Disney vacation”

We stayed here for almost 2 weeks, has everything you need, they are very quick to respond back to you if you have any issues or questions, the on site management were quick to get back to you also! …

3 BR | 2 BA | Sleeps 8 |

Distance to park: 10 miles to 9

  • Private pool

About this property

Vous serez accueilli et logé dans cette maison de vacances ayant 03 chambres et 02 salles de bains située seulement à 15 minutes en voiture de Walt Disney World ,dans un reel cul de sac vous procurant à coup sûr paix et tranquillité dans cette Communauté …

3 BR | 2 BA | Sleeps 6 |

Distance to park: 20 miles to Disney

  • Private pool

About this property

Kissimmee Villa


3 BR | 2.5 BA | Sleeps 6 |

  • Pool

About this property

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How Many Vacation Rentals Are Available Around Kissimmee

Our 2022 vacation rental listings offer a large selection of 26,207 house rentals around Kissimmee. From 19,452 house rentals to 4,987 villa rentals, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Kissimmee is on Vrbo.

When Is The Best Time To Stay In A Vacation Rental In Kissimmee

2145BMD: 6 Bedroom Vacation Villa Rental Kissimmee FL (136698)

Kissimmees busy season runs from March to August, with peak visitation periods taking place during U.S. Thanksgiving, Christmas, and Spring Break . During these times, Orlandos theme parks are teeming with fans of every age, and the states heat and humidity are at their peak. To avoid the worst of the heat, consider booking one of the areas vacation rentals for between October and March, when temperatures are a bit milder and the crowds have eased up slightly. Pack a light jacket or sweater to wear after the sun sets. The months of July through September are the rainy season in central Florida. Temperatures can often rise above 30 degrees Celsius, and afternoon thundershowers are a common occurrence, so be sure to have protective gear on hand.

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What Is The Best Area To Stay When Travelling To Kissimmee

Whether you’re travelling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Kissimmee:

  • Bellavida: 839 vacation rentals
  • Cumbrian Lakes: 137 vacation rentals
  • Venetian Bay Villages: 265 vacation rentals
  • Eagle Pointe South: 359 vacation rentals
  • Historic Downtown Kissimmee: 232 vacation rentals

For other neighbourhoods, please use our search bar to access the selection of vacation rentals available.

Getting Around Kissimmee From Your Vacation Rental

It’s easy to get around Kissimmee from your vacation home rental using the LYNX public transit system, an inexpensive bus service available throughout the entirety of Central Florida. The SunRail also serves the city and connects to the rest of the greater Orlando area. For shorter trips around town, you can hire taxis, ride-sharing services, or tour buses to see local attractions. Most hotels offer easy and convenient access to shuttle services as well. Or you can take the wheel by hiring a rental car and driving yourself from A to B.

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If You Are Notfully Vaccinated And Allowed To Travel To The United States By Air Through An Exception

You may be required to attest to some or all of the following measures, depending on the type of exception. For more information see Requirement for Proof of COVID-19 Vaccination for Air Passengers.

  • Get tested for current infection with a viral test 3-5 days after arrival, unless you have documentation of having recovered from COVID-19 in the past 90 days.
  • Stay at home or in your hotel room and self-quarantine for a full 5 days, even if you test negative, unless you have documentation of having recovered from COVID-19 in the past 90 days.
  • Isolate if your test result is positive or you develop COVID-19 symptoms.
  • If you intend to stay in the United States for 60 days or longer, become fully vaccinated against COVID-19 within 60 days of arriving in the United States or as soon as medically appropriate.

Outdoor Adventures In Kissimmee Fl

Windsor Hills Kissimmee Florida Vacation Rental Tour | Come See This Pretty Pool Home!

If you’re looking for an outdoor adventure or hoping for a bit of an adrenaline rush during your stay, you’re in luck! Tee off at Kissimmee golf courses, including the Remington Golf Club, or view the city by sky in a hot air balloon with Thompson Aire. Discover the Florida Everglades and alligators on an airboat ride with Boggy Creek Airboat Rides, an unforgettable experience that is guaranteed to amaze guests of all ages!

Invite your friends, pack your bags, and leave your worries behind when you come to one of our Kissimmee vacation homes. This charming town promises an exciting getaway full of adventure and family-friendly fun that you’ll remember for years to come.

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Day Trips From Kissimmee Fl

Our diverse selection of Kissimmee vacation rentals vary in size and included amenities, but each home boasts a location that is conveniently close to well-known family attractions like Walt Disney World Resort, SeaWorld, and Universal Orlando Resort! Spend your day exploring the parks or just seeing Orlando’s many sights, before heading back to your relaxing rental for a good night’s sleep.

During your stay, make sure to take some time and explore the surrounding area! Go pick citrus fruits in Haines City or shop at one of the many farmer’s markets, before heading back to your vacation rental to make a delicious homemade meal using local ingredients from the market. Cool off on a hot summer’s day with a splash at the water park in Reunion, only 15 miles away.

Florida Snowbird Rentals In The Sunshine State

Are you ready to trade a snow-white winter for a white-sand season along Floridas coastline? Warm days in the sun in Floridas subtropical climate will keep the winter blues at bay. Florida is known as the Sunshine State for good reason. Cities like St. Petersburg, Florida have an incredible 248 sunny days each year! Be sure to add sunscreen and sunglasses to your packing list as a Florida snowbird, when you book your next monthly rental.

Start planning your Florida snowbird vacation by browsing more than 1,200 unique rental properties listed by the American Snowbird Network of websites offered by The Snowbird Company. The Snowbird Company makes it easy to search for winter rentals and is designed to connect snowbirds and vacation rental owners.

Browse the selection of winter vacation rentals specifically priced for Florida snowbirds and multi-month reservations. Take advantage of off-season rates, great amenities and the ability to rent directl without additional service fees typically charged by other vacation rental websites. Find city center destinations, secluded hideaways and waterfront snowbird rentals all throughout Florida, from Atlantic Ocean beachside cities to the Florida Panhandle on the Gulf Coast.

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Before You Leave The United States

Make sure to plan ahead:

  • You tested positive for COVID-19.
  • Do not travel until a full 10 days after your symptoms started or the date your positive test was taken if you had no symptoms.
  • You are waiting for results of a COVID-19 test.
  • If your test comes back positive while you are at your destination, you will need to isolate and postpone your return until its safe for you to travel. Your travel companions may need to quarantine.
  • You had close contact with a person with COVID-19 and are recommended to quarantine.
  • Do not travel until a full 5 days after your last close contact with the person with COVID-19. It is best to avoid travel for a full 10 days after your last exposure.
  • If you must travel during days 6 through 10 after your last exposure:
  • Get tested at least 5 days after your last close contact. Make sure your test result is negative and you remain without symptoms before traveling. If you dont get tested, avoid travel until a full 10 days after your last close contact with a person with COVID-19.
  • Properly wear a well-fitting mask when you are around others for the entire duration of travel during days 6 through 10. If you are unable to wear a mask, you should not travel during days 6 through 10.
  • If you had close contact with a person with COVID-19 but are NOT recommended to quarantine

    Monthly Rentals Are Available Up To 6 Months

    7449Brook: 4 Bedroom Vacation Home Rental Kissimmee FL (137155)

    Flexcation is a trending idea that you can have a vacation anytime from anywhere while mixing work and play. But what about a Stretchcation or Staycation? If youre able to stretch your stay for longer youll discover that Orlando and the Central Florida Area have endless fun-filled things to do. By area, Florida isnt very large, so day-trips to surrounding places or the beach are completely doable. Explore more venture out! Take your time to find those hidden Florida gems and return to your vacation home each night.

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    Fine Food To Feast On Near Your Kissimmee Vacation Rental

    Kissimmee’s foodie scene combines international flavours with classic all-American diners in its diverse selection of restaurants. Treat your date to a romantic candlelit dinner in European-style bistros, or bring the whole family to a traditional steakhouse or a themed restaurant, where you can enjoy a medieval show with your meal. Asian restaurants can be found aplenty, offering fresh, authentic Japanese or Korean delicacies. Feeling adventurous? Try the spicier flavours served at the lively and colourful Mexican restaurants. Downtown Kissimmee has a cluster of bars and eateries if you feel like sampling a few different menus.

    Explore Kissimmee From Vacation Home Rentals

    Set just south of Orlando in Florida’s Osceola County, Kissimmee’s population has doubled twice since Walt Disney World opened nearby in 1971. Once a rural outpost where citrus groves and cattle ranches flourished, the city has maintained a sense of the past with a historic downtown, antique shops, and vintage amusement parks. Its sunny weather and wetlands make it a destination for anyone seeking warm temps, whether you prefer a weekend relaxing poolside or a more vigorous outdoor adventure. Its family attractions and close proximity to Disney make it a draw for the young and the young-at-heart.

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    Can I Rent Houses In Kissimmee

    Yes, of course. Vrbo has 19,461 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:

    • Villas: 4,991 rentals available
    • Resorts: 1,275 rentals available
    • Cabins: 61 rentals available

    But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

    Sights And Sounds Of Kissimmee

    Kissimmee is family travel paradise: 8 spots the perfect vacation rental

    Kissimmee’s Old Town is wonderful to stroll around for its many shops, restaurants, and bars. You will also be able to check out the Ferris wheel and a classic car show held over the weekends. From late February through early April, catch some Major League Baseball at the Osceola County Stadium.

    For insights into the restoration of WW2 aircrafts to working condition, visit the Warbird Air Museum. The Osceola County Historical Society is a traditional village and museum which features an interesting cracker house and horse stables. History buffs will enjoy a visit to the Museum of Military History which features the history of the American military experience through fun interactive exhibits.

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    Historic Sites Near Kissimmee Vacation Homes

    Kissimmee has numerous historic sites and museums to explore during your trip. Vacation rentals are available near fascinating places like the Museum of Military History, a museum with military relics, photographs, and personal stories, and Osceola County Welcome Center and History Museum, a local history museum with dioramas and interactive exhibits of the countys history. You can also visit the Monument of the States, a mid-century monument with stones sourced from the 50 states to celebrate American unity.

    Kissimmee Vacation Rentals Offer A Mix Of Leisure And Adventure

    If you’re thinking about spending a holiday in Florida, you can bet Kissimmee is one of the best places to visit. It’s been a holiday hotspot for decades, renowned for its sunshine and Southern hospitality. The addition of nearby world-famous theme parks in Orlando have turned the city into a launchpad to visit sites like Disney’s Hollywood Studios and Universal Parks & Resorts. By staying in Kissimmee, you get the bonus of maintaining some distance from larger crowds. You’ll find thousands of sleek villas with luxurious views and even more vacation home rentals that are perfect for the whole family.

    The name Kissimmee is shared with the river that flows through south-central Florida, and is debated to have stemmed from Native American origins. The town area was known as Allendale for a period of time, dedicated to a Confederate major who operated the first steamboat along the river. It was renamed Kissimmee after city incorporation in 1883. History buffs and military enthusiasts can get a kick out of the Museum of Military History, which details the past century of the American military experience. Many other historical sites and museums accessible from your vacation rental await in Kissimmee.

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    Monthly Vacation Rentals Apartment House In Kissimmee Fl

    Compare 36,588 available lakefront holiday vacation home properties, starts from $6

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    Activities Near Kissimmee Vacation Homes

    2707BOOK: Kissimmee FL 6 Bedroom Vacation Villa Rental (137256)

    Kissimmee’s historic downtown is the center of commercial life and offers a mix of family-owned businesses, shops, and restaurants. Consider a Kissimmee vacation rental within walking distance of Main Street, where you can enjoy breakfast at an outdoor cafe before deciding how you’ll take in the surrounding wetland wilderness. Eco-tours via horseback, zipline, or airboat are just a few of your options. You’ll likely have the chance to spot alligators, black bears, and dozens of bird species. Nighttime helicopter tours over the city provide a unique thrill, as the region’s theme park lights twinkle below.

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    Find Vacation Rentals In Or Near Kissimmee

    Discover more than 18637 vacation rentals in Kissimmee that are perfect for your next trip. Whether you are traveling with a group, family, friends, or couples retreat in Kissimmee, RBO has all types of rental properties with top amenities, including indoor/outdoor/private swimming pools, Wi-Fi, hot tubs, self-catering, and more.

    Rent By Owner offers vacation rentals near Kissimmee for all types of travelers, whether you are looking for a luxury home, villa, resort, condo, cabin, cottage, RV rental, or pet friendly accommodation in Kissimmee. Rent By Owner makes it easy to find and compare vacation rentals, matching you with rental properties from different vacation rental websites. By comparing these rental properties, RBO helps you find the best deals in Kissimmee. Luxury vacation rental prices start from $ 13 per night and affordable condos in Kissimmee start from $ 13 per night.

    RBO offers a large selection of vacation rentals from top leading sites such as, Airbnb, VRBO,, RV Share, Outdoorsy, and many more providers. Filter your search dates and discover Kissimmee vacation homes for your next trip.

    A Good Time To Visit Kissimmee

    Spring and summer are predictably peak seasons in Kissimmee, when college students descend for spring break in March/April, and when families with kids arrive between June and August. Be sure to book your Kissimmee vacation home well in advance during this period, so that you can ensure you find your perfect vacation rental. For a quieter time, late fall and winter are ideal, as the temperature can be anywhere between 47ºF and 84ºF.

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