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$ 64.

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.

Kissimmee Vacation Rentals from C$ 43/night

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Best Kissimmee vacation rentals

Irises House - private room in home

7 Good

C$ 64+

Parking

Free Wi-Fi

Pet friendly

Berkley Lake Townhomes

5.8 Fair

C$ 269+

Parking

Free Wi-Fi

Pool

Vacation Village At Parkway - Kissimmee - Pool

Vacation Village At Parkway

8 Very good

C$ 165+

Free Wi-Fi

High Point World Resort - Kissimmee - Living room

High Point World Resort

C$ 203+

Free Wi-Fi

Pool

Spa

Coastal Townhouse with Themed Bedroom at Reunion - Kissimmee - Balcony

Coastal Townhouse with Themed Bedroom at Reunion

C$ 481+

The Tropical Oaks Villa - Near Disney - Kissimmee - Pool

The Tropical Oaks Villa - Near Disney

5 Fair

C$ 167+

Free Wi-Fi

Pool

Sunset Palms Perfection | Near Attractions | Reunion Membership - Kissimmee - Living room

Sunset Palms Perfection | Near Attractions | Reunion Membership

C$ 397+

Paradise Palms by Florida Paradise - Kissimmee

Paradise Palms by Florida Paradise

C$ 273+

Free Wi-Fi

Cozy Master Room with Private Bath - Kissimmee

Cozy Master Room with Private Bath

8.2 Very good

C$ 131+

Parking

Free Wi-Fi

Pool

The Villas at Seven Dwarfs - Close to Disney - Kissimmee

The Villas at Seven Dwarfs - Close to Disney

8 Very good

C$ 248+

Parking

Free Wi-Fi

Runaway Beach Vacations - Kissimmee

Runaway Beach Vacations

8.4 Very good

C$ 330+

Free Wi-Fi

Pool

Holiday Villas of Kissimmee - Kissimmee

Holiday Villas of Kissimmee

8.1 Very good

C$ 223+

Parking

Free Wi-Fi

Pool

Three-Bedroom Townhome Kissimmee - Kissimmee

Three-Bedroom Townhome Kissimmee

8 Very good

C$ 232+

Parking

Free Wi-Fi

Pool

Three-Bedroom Apartment Kissimmee - Kissimmee

Three-Bedroom Apartment Kissimmee

9.3 Wonderful

C$ 231+

Parking

Free Wi-Fi

Pool

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

C$ 263+

Free Wi-Fi

Pool

Florida Deluxe Villas, Condos, & Homes - Kissimmee

Florida Deluxe Villas, Condos, & Homes

C$ 31+

Free Wi-Fi

Pool

Pet friendly

Spa

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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 July, with average rates of C$ 143. In comparison, December is the most expensive month, with prices at C$ 758.

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$ 166. The highest prices are found on Monday, with average rates at C$ 642.

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.

Find deals

Low season	July
High season	December
Average price (weeknight)	C$ 250
Average price (weekend night)	C$ 233

Cheapest month to stay with an average 56% drop in price.

Most expensive month to stay with an average 134% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

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.
Pet friendly, air-conditioned, pool, towels, hot tub, kitchen/kitchenette, parking, and linens are the most popular vacation rental property amenities in Kissimmee
Vacation rentals in Kissimmee are around 79% 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, 21 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.
Downtown is the neighborhood in Kissimmee with the most affordable vacation rental properties (156 properties with an average price of C$ 247 per night). Dream Vacation Homes, 1 BD Apt close to Disney/Universal/Shopping/Dining, and Vacation Homes By Orlando Fun Rentals are the most popular rental properties in Downtown.
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 July and May.
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$ 418.

See more tips

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$ 64. 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.