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Kissimmee vacation rentals

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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
Irises House - private room in home
Kissimmee, FL, United States
7.2Good(70)
Parking
Free Wi-Fi
Pet friendly
C$ 64+
Check availability
Berkley Lake Townhomes - Kissimmee - Pool
Berkley Lake Townhomes
Kissimmee, FL, United States
5.8Fair(1241)
Parking
Free Wi-Fi
Pool
C$ 268+
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Vacation Village At Parkway - Kissimmee - Pool
Vacation Village At Parkway
Kissimmee, FL, United States
8.0Very good(730)
Free Wi-Fi
C$ 148+
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High Point World Resort - Kissimmee - Living room
High Point World Resort
Kissimmee, FL, United States
Free Wi-Fi
Pool
Spa
C$ 202+
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Coastal Townhouse with Themed Bedroom at Reunion - Kissimmee - Balcony
Coastal Townhouse with Themed Bedroom at Reunion
Kissimmee, FL, United States
C$ 476+
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The Tropical Oaks Villa - Near Disney - Kissimmee - Pool
The Tropical Oaks Villa - Near Disney
Kissimmee, FL, United States
5.0Fair(21)
Free Wi-Fi
Pool
C$ 166+
Check availability
Sunset Palms Perfection | Near Attractions | Reunion Membership - Kissimmee - Living room
Sunset Palms Perfection | Near Attractions | Reunion Membership
Kissimmee, FL, United States
C$ 406+
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Paradise Palms by Florida Paradise - Kissimmee
Paradise Palms by Florida Paradise
Kissimmee, FL, United States
Free Wi-Fi
C$ 272+
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Cozy Master Room with Private Bath - Kissimmee
Cozy Master Room with Private Bath
Kissimmee, FL, United States
8.0Very good(31)
Parking
Free Wi-Fi
Pool
C$ 132+
Check availability
The Villas at Seven Dwarfs - Close to Disney - Kissimmee
The Villas at Seven Dwarfs - Close to Disney
Kissimmee, FL, United States
8.0Very good(308)
Parking
Free Wi-Fi
C$ 255+
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Runaway Beach Vacations - Kissimmee
Runaway Beach Vacations
Kissimmee, FL, United States
8.4Very good(12)
Free Wi-Fi
Pool
C$ 328+
Check availability
Holiday Villas of Kissimmee - Kissimmee
Holiday Villas of Kissimmee
Kissimmee, FL, United States
8.1Very good(90)
Parking
Free Wi-Fi
Pool
C$ 220+
Check availability
Three-Bedroom Townhome Kissimmee - Kissimmee
Three-Bedroom Townhome Kissimmee
Kissimmee, FL, United States
8.0Very good(20)
Parking
Free Wi-Fi
Pool
C$ 228+
Check availability
Three-Bedroom Apartment Kissimmee - Kissimmee
Three-Bedroom Apartment Kissimmee
Kissimmee, FL, United States
9.3Wonderful(82)
Parking
Free Wi-Fi
Pool
C$ 227+
Check availability
5 Bedroom 4 Bath Paradise Palms Town Home With A Lake View - Kissimmee
5 Bedroom 4 Bath Paradise Palms Town Home With A Lake View
Kissimmee, FL, United States
Free Wi-Fi
Pool
C$ 262+
Check availability
Florida Deluxe Villas, Condos, & Homes - Kissimmee
Florida Deluxe Villas, Condos, & Homes
Kissimmee, FL, United States
Free Wi-Fi
Pool
Pet friendly
Spa
C$ 30+
Check availability
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KAYAK’s insights for vacation rentals in Kissimmee

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Kissimmee with confidence.

Which month has the cheapest vacation rental rates in Kissimmee?

Vacation rentals are cheapest in Kissimmee in May, with average rates of C$ 121. In comparison, December is the most expensive month, with prices at C$ 752.

What is the cheapest day of the week to book a vacation rental in Kissimmee?

Saturday offers the lowest rates in Kissimmee, with an average nightly price of C$ 165. The highest prices are found on Monday, with average rates at C$ 636.

How early should you book a vacation rental in Kissimmee?

Book at least 19 days before your stay begins to get the best price for your Kissimmee vacation rental.
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Good to know

Low season

May

High season

December

Average price (weeknight)

C$ 249

Average price (weekend night)

C$ 232
Cheapest month to stay with an average 65% drop in price.
Most expensive month to stay with an average 120% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Kissimmee holiday 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, air-conditioned, pet friendly, towels, hot tub, kitchen/kitchenette, parking, and linens are the most popular vacation rental property amenities in Kissimmee
  • Vacation rentals in Kissimmee are around 25% 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 Private Vacational Cozy Suite (9.5, 23 reviews), New Home Near Disney Bliss! (9.4, 48), and Dazzling Newly Renovated Condo 1.5 miles to Disney (9.3, 27), 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 May and July.
  • The cheapest night for renting a vacation home in Kissimmee is Saturday. In contrast, the most expensive is Monday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Kissimmee for 8 days.
  • The cheapest Kissimmee vacation rental found on KAYAK in the last 2 weeks was C$ 101, while the most expensive was C$ 416.
See more tips

FAQs when booking a vacation home in Kissimmee

  • 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 agritourism, apartments, cabins, caravans, condos, cottages, houses, vacation villages, homestays and villas.

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

    There are a number of dog and pet-friendly Kissimmee vacation rentals, with around 6% allowing you to bring your pet along with you.

  • 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 C$ 63. Search here for similar prices

  • How much is a vacation rental in Kissimmee for this weekend?

    In the last 72 hours, users have found Kissimmee vacation rentals for this weekend for as low as C$ 60 per night. 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.

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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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Vacation rentals by topic

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Three-Bedroom Apartment Kissimmee - Kissimmee
Three-Bedroom Apartment Kissimmee
Kissimmee, FL, United States
9.3Wonderful(82)
Parking
C$ 226+
Check availability
Laguna Villas - Kissimmee
Laguna Villas
Kissimmee, FL, United States
7.8Good(559)
Parking
C$ 199+
Check availability
Celebration Suites - Kissimmee
Celebration Suites
Kissimmee, FL, United States
9.1Wonderful(5192)
Parking
C$ 197+
Check availability
Stunning 4 Bd w/ GameRoom Close to Disney 5110K - Kissimmee
Stunning 4 Bd w/ GameRoom Close to Disney 5110K
Kissimmee, FL, United States
7.9Good(20)
Parking
C$ 363+
Check availability
Bikini on the Beach at Terra Verde Resort - Kissimmee
Bikini on the Beach at Terra Verde Resort
Kissimmee, FL, United States
6.4Okay(6)
Parking
C$ 399+
Check availability
Heatherlake Villa, Close To Disney - Kissimmee
Heatherlake Villa, Close To Disney
Kissimmee, FL, United States
Parking
C$ 439+
Check availability
Beautiful Townhome Old Town - Kissimmee
Beautiful Townhome Old Town
Kissimmee, FL, United States
Parking
C$ 378+
Check availability
Four Bedrooms At Storeylakeresort 3063 - Kissimmee
Four Bedrooms At Storeylakeresort 3063
Kissimmee, FL, United States
8.0Very good(73)
Parking
C$ 353+
Check availability
Stunning Lakeview Townhome w Private Pool - Kissimmee
Stunning Lakeview Townhome w Private Pool
Kissimmee, FL, United States
6.8Okay(6)
Parking
C$ 447+
Check availability
Four Bedrooms Townhome 4861 - Kissimmee
Four Bedrooms Townhome 4861
Kissimmee, FL, United States
8.4Very good(33)
Parking
C$ 385+
Check availability
Beautiful Single Vacation Home Sl4788 - Kissimmee
Beautiful Single Vacation Home Sl4788
Kissimmee, FL, United States
10Wonderful(7)
Parking
C$ 626+
Check availability
Dws Vacation Villas - Kissimmee
Dws Vacation Villas
Kissimmee, FL, United States
8.3Very good(321)
Parking
C$ 443+
Check availability
Five Bedrooms Home with Pool 4851 - Kissimmee
Five Bedrooms Home with Pool 4851
Kissimmee, FL, United States
7.9Good(40)
Parking
C$ 460+
Check availability
Four Bedrooms With Screen Poolstoreylake 4910 - Kissimmee
Four Bedrooms With Screen Poolstoreylake 4910
Kissimmee, FL, United States
9.8Wonderful(25)
Parking
C$ 469+
Check availability
3 Bedroom Resort Style Condo, 3 Miles to Disney! - Kissimmee
3 Bedroom Resort Style Condo, 3 Miles to Disney!
Kissimmee, FL, United States
9.2Wonderful(57)
Parking
C$ 291+
Check availability
Orlando House Disney Area - Kissimmee
Orlando House Disney Area
Kissimmee, FL, United States
8.5Very good(208)
Parking
C$ 282+
Check availability
Florida Villa - Kissimmee
Florida Villa
Kissimmee, FL, United States
9.3Wonderful(61)
Parking
C$ 262+
Check availability

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Everything you need to know for your stay in Kissimmee

Kissimmee vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Kissimmee. Find cheap vacation homes to rent in Kissimmee. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Kissimmee that suits you best.

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