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Kissimmee vacation rentals

Thu 5/23
Fri 5/24

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Best Kissimmee vacation rentals

Most recommended vacation rentals in Kissimmee

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Irises House - private room in home - Kissimmee - Kitchen
Free Wi-Fi
Pet friendly
Berkley Lake Townhomes - Kissimmee - Pool
Free Wi-Fi
Private Pool Homes
6.8 Okay
Free Wi-Fi

Good to know

Low season


High season


Average price (weeknight)


Average price (weekend night)

Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 63% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a vacation rental in Kissimmee

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Kissimmee vacation rental deals

  • If you are a golf enthusiast, consider checking out Kissimmee vacation rentals in Reunion. This neighborhood is popular for golf, with the Reunion Resort hosting three PGA golf courses, including Arnold Palmer, Tom Watson, and Jack Nicklaus golf courses. Checking in at Great Three Beds Vacation Apartment with balcony at Reunion Resort is recommended.
  • If you are looking to enjoy the Kissimmee shopping experience, consider staying at Kissimmee vacation rentals in downtown Kissimmee. This neighborhood is home to Lanier's Historic Downtown Marketplace and the Kissimmee Valley Farmers' Market, which are ideal for an exciting shopping spree. Staying at 4 bedroom villa, accommodates 10 guests places you within walking distance to the major shopping outlets in downtown Kissimmee.
  • If you are looking for a peaceful and quiet stay, consider checking in at vacation rentals at Celebration, such as at Celebration Suites - 2 Bedroom Condos. This neighborhood is recommended if you need to escape the bustling Kissimmee downtown or simply enjoy a calm, relaxing afternoon at the theme parks. 
  • For business travelers, consider staying at Hapimag Orlando at Lake Berkley. This vacation rental is primely situated at the heart of Kissimmee, offering you convenient access to the city's business hub. Also, the establishment features access to a computer, a business center, and free parking, great for business travelers.
  • For travelers seeking to keep fit during their stay, consider looking for Kissimmee house rentals with fitness services. The Town Home and Villas At Seven Dwarfs Resort will be a good fit for you. This rental home features a well-equipped fitness center, with equipment like weights, treadmills, bikes, and resistance bands, great for maintaining your fitness routine even when on vacation.
  • Pool is the most popular vacation rental property amenity in Kissimmee
  • Vacation rentals in Kissimmee are around 67% more expensive than hotels on average. Search here to compare prices for all accommodation types in Kissimmee.
  • The best vacation rental properties in Kissimmee are Upscale Kissimmee Vacation Rental with Private Pool! (9.8, 29 reviews), Bahama Bay, Davenport, Florida Oversize 2 Br condo (9.3, 51), and Magic Village 4 Bedroom! Welcome Home! (9.2, 34), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Kissimmee, you should consider visiting during the low season. The cheapest vacation homes in Kissimmee can be found in February and May.
  • The cheapest night for renting a vacation home in Kissimmee is Tuesday. In contrast, the most expensive is Sunday.
  • Book your Kissimmee vacation rental more than 90 days before your stay begins to get the best price.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Kissimmee for 5 days.
  • The cheapest Kissimmee vacation rental found on KAYAK in the last 2 weeks was $42, while the most expensive was $318.

FAQs when booking a vacation home in Kissimmee

  • How much is a vacation rental for a week in Kissimmee?

    The average price for a weekly Kissimmee vacation rental found by KAYAK users in the last 2 weeks is $3,173.

  • How much is a vacation rental for a month in Kissimmee?

    The average price for a monthly Kissimmee vacation rental found by KAYAK users in the last 2 weeks is $13,599.

  • What types of vacation rentals are available in Kissimmee?

    There are loads of different property types that you can make your vacation home in Kissimmee. You’ll find apartments, condos, cottages, houses, holiday parks, homestays and villas.

  • What are some of the most-loved vacation rentals available in Kissimmee?

    There are many types of properties available for Kissimmee vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are The Villas At Seven Dwarfs Lane and Westgate Town Center Resort.

  • Are there any pet-friendly vacation rentals in Kissimmee?

    There are a number of dog and pet-friendly Kissimmee vacation rentals, with around 5% allowing you to bring your pet along with you.

  • How much is a vacation rental in Kissimmee?

    KAYAK users have found vacation rentals in Kissimmee for as cheap as $146 in the last 3 days. The average price is $453.

  • How much is a vacation rental in Kissimmee for tonight?

    In the last 72 hours, users have found Kissimmee vacation rentals for tonight for as low as $266. Search here for similar prices

  • How can I find vacation rentals near me in Kissimmee?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Which Kissimmee vacation rentals allow pets?

    If you seek pet-friendly vacation rentals in Kissimmee, consider checking in at A Perfect Place to Stay or Vacation USA. Both vacation rentals allow pets into the property, saving you the inconvenience of leaving your four-legged buddy behind. However, you should inform your vacation rental in advance about your vacation plans.

  • Which vacation rentals in Kissimmee have a pool?

    Various Kissimmee vacation rentals have swimming pools on-site, including Four Bedrooms Townhome 5126 and Beautiful 3 bed/2 bath condo near major attractions. Both vacation rental swimming pools are accessible all year, ideal for unwinding after an exciting day of touring Kissimmee.

  • Which Kissimmee vacation rentals are close to dining options?

    If you are looking to explore the cuisine in Kissimmee, consider staying around Dakin Avenue. This avenue hosts some of the city's finest restaurants and eateries, including 3 Sisters Speakeasy and Willy's Wieners. Lucaya Village Resort 1503 a 3 bedroom vacation home that will offer you convenient access to most dining options in Kissimmee.

  • Which is the best vacation rental for families in Kissimmee?

    If you are traveling with your family, consider booking a Luxury Three Bedroom Condo near Disney World reservation. This vacation rental is spacious enough to accommodate 6-8 guests, ideal for family staycations. Moreover, this property features various family-friendly amenities onsite, including a furnished kitchen, kids' outdoor equipment, and a barbeque.

Where to stay in Kissimmee?

Our map will help you find the perfect place to stay in Kissimmee by showing you the exact location of each vacation rental.

What Kissimmee vacation rental guests are talking about

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What Kissimmee vacation rental guests are talking about

Vacation rentals by topic

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Three-Bedroom Apartment Kissimmee - Kissimmee
The Tropical Oaks Villa - Near Disney - Kissimmee
Florida Villa
9.3 Wonderful

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