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Kissimmee holiday 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
Air conditioning
€40+
Check availability
Berkley Lake Townhomes - Kissimmee - Pool
Berkley Lake Townhomes
Kissimmee, FL, United States
5.8Fair(1241)
Parking
Free Wi-Fi
Pool
Air conditioning
€170+
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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
Air conditioning
€94+
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High Point World Resort - Kissimmee - Living room
High Point World Resort
Kissimmee, FL, United States
Free Wi-Fi
Pool
Air conditioning
€128+
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Coastal Townhouse with Themed Bedroom at Reunion - Kissimmee - Balcony
Coastal Townhouse with Themed Bedroom at Reunion
Kissimmee, FL, United States
Air conditioning
€302+
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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
Air conditioning
€105+
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Sunset Palms Perfection | Near Attractions | Reunion Membership - Kissimmee - Living room
Sunset Palms Perfection | Near Attractions | Reunion Membership
Kissimmee, FL, United States
Air conditioning
€257+
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Paradise Palms by Florida Paradise - Kissimmee
Paradise Palms by Florida Paradise
Kissimmee, FL, United States
Free Wi-Fi
€172+
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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
Air conditioning
€84+
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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
Air conditioning
€162+
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Runaway Beach Vacations - Kissimmee
Runaway Beach Vacations
Kissimmee, FL, United States
8.4Very Good(12)
Free Wi-Fi
Pool
Air conditioning
€208+
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Holiday Villas of Kissimmee - Kissimmee
Holiday Villas of Kissimmee
Kissimmee, FL, United States
8.1Very Good(90)
Parking
Free Wi-Fi
Pool
Air conditioning
€139+
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Three-Bedroom Townhome Kissimmee - Kissimmee
Three-Bedroom Townhome Kissimmee
Kissimmee, FL, United States
8.0Very Good(20)
Parking
Free Wi-Fi
Pool
Air conditioning
€145+
Check availability
Three-Bedroom Apartment Kissimmee - Kissimmee
Three-Bedroom Apartment Kissimmee
Kissimmee, FL, United States
9.3Wonderful(82)
Parking
Free Wi-Fi
Pool
Air conditioning
€144+
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
€166+
Check availability
Florida Deluxe Villas, Condos, & Homes - Kissimmee
Florida Deluxe Villas, Condos, & Homes
Kissimmee, FL, United States
Free Wi-Fi
Pool
Pet friendly
Air conditioning
€19+
Check availability
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KAYAK’s insights for holiday 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 October, with average rates of €86. In comparison, December is the most expensive month, with prices at €198.

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

Sunday offers the lowest rates in Kissimmee, with an average nightly price of €83. The highest prices are found on Saturday, with average rates at €189.

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

April

High season

February

Average price (weekend night)

€174
Cheapest month to stay with an average 36% drop in price.
Most expensive month to stay with an average 36% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Kissimmee holiday rental deals

  • If you’re wanting accommodation in Old Town then consider staying at the Great Family Town Home w/Resort Facilities close to Disney, Dining & Shops. The accommodation is located in the heart of Old Town and has lots of amenities for guests to enjoy. The house sleeps up to eight guests and is equipped with four bedrooms and four bathrooms.
  • Visiting Kissimmee in a couple? Consider staying at the adult-only accommodation and Kissimmee holiday rental and condo 116 Serine Poolside at Parkway Palms. Guests can find themselves enjoying the parking and Wi-Fi that’s available during their stay. It’s the perfect choice for a private and romantic getaway.
  • The four-star Disney’s Beach Club Resort is a great choice of stay for your time in Kissimmee. Those who stay here can expect free Wi-Fi and also a free airport shuttle service if you’re looking for stress-free travel from the airport.
  • If you’re visiting with children then consider staying at the Kissimme holiday rental Disney’s Boardwalk Inn. This four-star accommodation comes with pool access and guests can find themselves within four miles of Walt Disney World, which is guaranteed to give your children hours of fun.
  • Those who are looking for the optimal luxury on their trip to Kissimmee should consider staying at the five-star 3109 Storey Lake Resort 41270/44281. Guests that stay here should expect exceptional service, use of all large pools, as well as free parking and free Wi-Fi.
  • Pool, air-conditioned, pet friendly, towels, hot tub, kitchen/kitchenette, parking, and linens are the most popular holiday rental property amenities in Kissimmee
  • Holiday 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 holiday 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 travellers.
  • If you’re looking for a cheap holiday rental in Kissimmee, you should consider visiting during the low season. The cheapest holiday homes in Kissimmee can be found in April and February.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Kissimmee for 6 days.
See more tips

FAQs when booking a holiday home in Kissimmee

  • What types of holiday rentals are available in Kissimmee?

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

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

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

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

    In the last 72 hours, users have found Kissimmee holiday rentals for tonight for as low as €40. Search here for similar prices

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

    In the last 72 hours, users have found Kissimmee holiday rentals for this weekend for as low as €38 per night. Search here for similar prices

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

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

  • If I want accommodation in Kissimmee city centre, where should I stay?

    Those wanting to be located in the heart of Kissimmee with only a short 0.1-mile walk from the city centre should consider staying at the Kissimmee holiday home Homes4uu – Disney Area Vacation Homes. The house sleeps up to ten guests and is also equipped with an outdoor pool and a fully equipped kitchen. Also, enjoy the use of free parking and Wi-Fi available on request.

  • Where should I stay if I want to be near Walt Disney World?

    Consider staying at the four-star Disney’s Contemporary Resort, if you’re wanting to be in close proximity to the attraction of Walt Disney World. The accommodation is only located 0.4 miles away. Guests can also find themselves located near the airport, as well as within three miles of Disney’s Magnolia Golf Course and Beachcomber Beach. Magic Kingdom Park is also only six miles away from this accommodation.

  • Where can I stay if I’m visiting Kissimmee in a group?

    If you’re looking for a choice of a Kissimmee house rental that can accommodate up to eight guests, then consider staying at the Villa Palmera. The accommodation is equipped with four bedrooms and three bathrooms. Guests will also find Wi-Fi and parking that’s free of charge during their stay.

  • If I’m visiting Kissimmee on a budget, where can I stay?

    Consider staying at the Kissimmee holiday rental apartment Convenience At Its Best. The apartment is budget friendly and sleeps up to six guests. Those that are staying here will find themselves nearby the landmarks of Lake Tohopekaliga and also Old Town. The accommodation is equipped with a fully functional kitchen.

See more FAQs

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 holiday rental.

What Kissimmee holiday rental guests are talking about

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Holiday rentals by topic

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Three-Bedroom Apartment Kissimmee - Kissimmee
Three-Bedroom Apartment Kissimmee
Kissimmee, FL, United States
9.3Wonderful(82)
Parking
€144+
Check availability
Laguna Villas - Kissimmee
Laguna Villas
Kissimmee, FL, United States
7.8Good(559)
Parking
€126+
Check availability
Celebration Suites - Kissimmee
Celebration Suites
Kissimmee, FL, United States
9.1Wonderful(5191)
Parking
€128+
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
€228+
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
€255+
Check availability
Heatherlake Villa, Close To Disney - Kissimmee
Heatherlake Villa, Close To Disney
Kissimmee, FL, United States
Parking
€281+
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Beautiful Townhome Old Town - Kissimmee
Beautiful Townhome Old Town
Kissimmee, FL, United States
Parking
€241+
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Four Bedrooms At Storeylakeresort 3063 - Kissimmee
Four Bedrooms At Storeylakeresort 3063
Kissimmee, FL, United States
8.0Very Good(73)
Parking
€222+
Check availability
Stunning Lakeview Townhome w Private Pool - Kissimmee
Stunning Lakeview Townhome w Private Pool
Kissimmee, FL, United States
6.8Okay(6)
Parking
€284+
Check availability
Four Bedrooms Townhome 4861 - Kissimmee
Four Bedrooms Townhome 4861
Kissimmee, FL, United States
8.4Very Good(33)
Parking
€247+
Check availability
Beautiful Single Vacation Home Sl4788 - Kissimmee
Beautiful Single Vacation Home Sl4788
Kissimmee, FL, United States
10Wonderful(7)
Parking
€403+
Check availability
Dws Vacation Villas - Kissimmee
Dws Vacation Villas
Kissimmee, FL, United States
8.3Very Good(321)
Parking
€279+
Check availability
Five Bedrooms Home with Pool 4851 - Kissimmee
Five Bedrooms Home with Pool 4851
Kissimmee, FL, United States
7.9Good(40)
Parking
€298+
Check availability
Four Bedrooms With Screen Poolstoreylake 4910 - Kissimmee
Four Bedrooms With Screen Poolstoreylake 4910
Kissimmee, FL, United States
9.8Wonderful(25)
Parking
€291+
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
€185+
Check availability
Orlando House Disney Area - Kissimmee
Orlando House Disney Area
Kissimmee, FL, United States
8.5Very Good(208)
Parking
€178+
Check availability
Florida Villa - Kissimmee
Florida Villa
Kissimmee, FL, United States
9.3Wonderful(61)
Parking
€166+
Check availability

Popular topics

Everything you need to know for your stay in Kissimmee

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

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