Kissimmee vacation rentals

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Booking Insights
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Best Kissimmee vacation rentals

Family Friendly & Clean - Private Pool & Hot Tub. Near Disney! 4br 3ba Wifi - Kissimmee - Pool
Family Friendly & Clean - Private Pool & Hot Tub. Near Disney! 4br 3ba Wifi
Kissimmee, FL, United States
10Wonderful(3)
House
Pool
C$ 471+
Check availability
Updated Condo, 5 mi to Disney, On-site Water Park - Kissimmee - Pool
Updated Condo, 5 mi to Disney, On-site Water Park
Kissimmee, FL, United States
9.0Wonderful(25)
Apartment
Parking
Free Wi-Fi
Pool
C$ 400+
Check availability
Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly! - Kissimmee - Living room
Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly!
Kissimmee, FL, United States
9.7Wonderful(93)
House
Free Wi-Fi
Pool
C$ 265+
Check availability
Great And Practical Townhouse In Gated Community, Sleeps 6 10 Min To Disney! - Bay Lake - Building
Great And Practical Townhouse In Gated Community, Sleeps 6 10 Min To Disney!
Bay Lake, FL, United States
8.6Very good(22)
House
Parking
Free Wi-Fi
C$ 303+
Check availability
Cozy Townhome near Orlando's Themeparks with private Jacuzzi & heated Pool - Kissimmee - Bedroom
Cozy Townhome near Orlando's Themeparks with private Jacuzzi & heated Pool
Kissimmee, FL, United States
8.4Very good(41)
House
Free Wi-Fi
Pool
C$ 255+
Check availability
H - New 2 Bedroom Condo - 5 Miles to Disney - Free Water Park - Kissimmee - Living room
H - New 2 Bedroom Condo - 5 Miles to Disney - Free Water Park
Kissimmee, FL, United States
9.2Wonderful(19)
Apartment
Parking
Free Wi-Fi
Pool
C$ 270+
Check availability
Magic Village 4 Bedroom! Welcome Home! - Kissimmee - Living room
Magic Village 4 Bedroom! Welcome Home!
Kissimmee, FL, United States
8.8Very good(42)
House
Parking
Free Wi-Fi
Pool
C$ 558+
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Only 5 Miles from Disney! Free Water Park! 2 Bed, 2 Bath Condo, Sleeps 8 - Kissimmee - Pool
Only 5 Miles from Disney! Free Water Park! 2 Bed, 2 Bath Condo, Sleeps 8
Kissimmee, FL, United States
9.4Wonderful(57)
Condo
Parking
Free Wi-Fi
Pool
C$ 337+
Check availability
6br Luxury Villa: Pool, Spa, Game Room & Disney Magic 2957 Fs - Kissimmee - Dining room
6br Luxury Villa: Pool, Spa, Game Room & Disney Magic 2957 Fs
Kissimmee, FL, United States
8.4Very good(39)
House
C$ 519+
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Beautiful house great location private pool - Kissimmee - Bedroom
Beautiful house great location private pool
Kissimmee, FL, United States
8.2Very good(10)
House
Parking
Free Wi-Fi
Pool
C$ 391+
Check availability
Four Bedrooms Home with Pool 3079 - Kissimmee - Living room
Four Bedrooms Home with Pool 3079
Kissimmee, FL, United States
10Wonderful(45)
House
Parking
Free Wi-Fi
Pool
Spa
C$ 467+
Check availability
Welcome To Storey Lake Resort - Minutes From Disney, 5br And 4 Ba - Kissimmee - Dining room
Welcome To Storey Lake Resort - Minutes From Disney, 5br And 4 Ba
Kissimmee, FL, United States
9.6Wonderful(26)
House
Free Wi-Fi
C$ 485+
Check availability
Ground floor spacious house 4BR VP2512 - Kissimmee
Ground floor spacious house 4BR VP2512
Kissimmee, FL, United States
8.7Very good(20)
House
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 465+
Check availability
Splendid Thematic 2BR with Waterpark - Kissimmee
Splendid Thematic 2BR with Waterpark
Kissimmee, FL, United States
9.6Wonderful(22)
Apartment
Parking
Free Wi-Fi
Pool
Spa
C$ 374+
Check availability
3840 Supreme Villa 6Bd Private Pool and Game Room - Kissimmee
3840 Supreme Villa 6Bd Private Pool and Game Room
Kissimmee, FL, United States
8.9Very good(26)
House
Parking
Free Wi-Fi
Pool
Spa
C$ 555+
Check availability
Disney Villa Magical Retreat Private Pool, Lakeview & Game Room - Kissimmee
Disney Villa Magical Retreat Private Pool, Lakeview & Game Room
Kissimmee, FL, United States
9.9Wonderful(23)
Villa
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 407+
Check availability
Booking Insights

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 August, with average rates of C$ 130. In comparison, December is the most expensive month, with prices at C$ 338.

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 C$ 137. The highest prices are found on Saturday, with average rates at C$ 224.

How early should you book a vacation rental in Kissimmee?

Book at least 25 days before your stay begins to get the best price for your Kissimmee vacation rental.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
July
C$ 157
C$ 189
Cheapest month to stay with an average 29% drop in price.
Most expensive month to stay with an average 36% 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, kitchen/kitchenette, air-conditioned, hot tub, parking, pet friendly, and wifi are the most popular vacation rental property amenities in Kissimmee
  • Vacation rentals in Kissimmee are around 66% 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 Four Bedrooms Home with Pool 3079 (10.0, 45 reviews), Disney Villa Magical Retreat Private Pool, Lakeview & Game Room (9.9, 23), and Close to Disney! NO Extra Fees! Gated! Clean & Comfy! Family Friendly! (9.7, 93), 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 January and February.
  • The cheapest night for renting a vacation home in Kissimmee is Monday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Kissimmee for 11 days.
  • The cheapest Kissimmee vacation rental found on KAYAK in the last 2 weeks was C$ 409, while the most expensive was C$ 409.

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 C$ 1,033.

  • 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 C$ 4,427.

  • 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, aparthotels, 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 4% 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$ 75. 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$ 67 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.

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.

Everything you need to know for your stay in Kissimmee