Kissimmee holiday rentals

We found 31,413 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Kissimmee by choosing from 1616 houses, 82 apartments and other holiday rentals. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Kissimmee

Showing deals for:23 Oct - 30 Oct

Image gallery for Solar aligned | South Facing Pool | 6' 6" King Bed | 400Mb Fibre | Disney-22mins

Living Area, access to front door and pool.
9.8 out of 10, Exceptional, (112 reviews)
Exceptional
(112 reviews)

Solar aligned | South Facing Pool | 6' 6" King Bed | 400Mb Fibre | Disney-22mins

Clermont

8% off
Price is AU$3,045
for 7 nights, 1 villa
AU$435 per night
includes taxes & fees
Solar aligned | South Facing Pool | 6' 6" King Bed | 400Mb Fibre | Disney-22mins

Find spaces that suit your style

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Kissimmee

  • Family-friendly attractions: Enjoy a variety of amusement parks and outdoor activities that cater to visitors of all ages.
  • Natural splendour: Discover beautiful lakes and scenic landscapes ideal for leisurely explorations.
  • Cultural encounters: Immerse in local charm and vibrant neighbourhoods offering unique experiences.
  • Sunny weather: Relish the warm climate perfect for outdoor adventures year-round.
  • Convenient location: Benefit from Kissimmee’s proximity to key landmarks and entertainment hubs.

Popular types of accommodation in Kissimmee

Discover Kissimmee, Florida – a vibrant city offering an array of holiday rentals, including private holiday homes, villas, and condos, set against a backdrop of captivating local attractions and landmarks. Enjoy beach access and explore the city’s unique experiences, ensuring a memorable getaway for all travellers. Whether you’re searching for apartment rentals or a Miami holiday rental experience, Kissimmee provides transparent, customer-centric holiday solutions tailored for Australia travellers.

  • Private Holiday Homes: Most travellers prefer exclusive, self-catering homes providing privacy and ample space for a family-friendly stay.
  • Villas: A popular choice offering upscale, private retreats with luxurious amenities for an indulgent holiday experience.
  • Condos: Ideal for groups, these modern, compact units blend comfort with convenience in a secure setting.
  • Apartments: Efficient, urban-style lodgings that offer a cosy, independent living option during your visit.
  • Cottages: Charming, quaint dwellings that evoke a cosy, rustic ambience for a relaxed getaway.**

Top attractions in and around Kissimmee

Kissimmee, Florida, is a vibrant city perfect for family holidays and entertainment-themed adventures. Visitors can enjoy a variety of attractions, including thrilling theme parks and beautiful lakes, offering outdoor activities and cultural experiences. This lively destination caters to those seeking fun-filled days, whether at amusement parks or exploring the natural beauty surrounding the area, ensuring memorable experiences for everyone.

  • Lake Cecile: A picturesque lake offering stunning scenery, perfect for outdoor activities. Enjoy a relaxing day by the beach or take part in romantic picnics amidst nature.
  • Universal Studios Florida: Although located 21km away, this famous theme park provides thrilling entertainment and family-friendly attractions, making it a must-visit for adventure lovers.
  • Universal CityWalk: Also 21km away, this vibrant tourist precinct features lively outdoor spaces, dining, and entertainment options, ideal for families looking to unwind after a day of exploration.

Things to do recommended for couples

Looking for a romantic getaway in Kissimmee? Enjoy a sunset airboat tour through the enchanting Everglades, or indulge in a candlelit dinner at a charming lakeside restaurant. Don't miss a leisurely stroll through Old Town, where the vibrant atmosphere sets the perfect backdrop for love.

Things to do recommended for families

Families will delight in the thrilling attractions of the Kissimmee area, such as the interactive experiences at Gatorland, the magical world of Walt Disney World, or the adventure-filled days at Fun Spot America, ensuring unforgettable memories for all ages.

Things to do recommended for groups

Experience local charm in Kissimmee with group-friendly activities like exploring the vibrant downtown, enjoying live music, and indulging in traditional American barbecue, all while appreciating the scenic beauty of Florida's landscape.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Kissimmee

When travelling with a group, family, pets, or seeking extended stays, it's essential to filter your options based on your specific priorities. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Stayz.
  • Traveling to Kissimmee with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kissimmee: For some, a family holiday isn’t complete without their four-legged companion in tow. If this resonates with you, then explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds so that everyone feels right at home.
  • Planning for a long term stay visiting Kissimmee: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the ideal destination. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Kissimmee

Discover Kissimmee’s charm with family-friendly attractions and vibrant neighbourhoods. Enjoy the warm sunny weather and explore unique experiences like the cosy fireplace spots and scenic Disney Lake. Ideal for both business and leisure, the city offers fantastic opportunities for romantic escapades and memorable excursions, all from a prime location close to Disney Springs and other key landmarks. Let Kissimmee be your destination for a well-rounded holiday experience.

  • Orlando: Orlando, a vibrant metropolis, envelops Kissimmee with its dynamic energy. The city is renowned for offering a diverse palette of travel experiences, including family-friendly attractions, entertainment-themed escapades, and business-focused engagements. Visitors can explore a variety of venues such as expansive shopping areas, arts centres, and recreational hubs. The area’s proximity to renowned theme parks, film studios, and coastal beaches ensures that every traveller finds something to spark their interest.
  • Four Corners: Four Corners is a charming village located in the vicinity of Kissimmee. It invites families, entertainment enthusiasts, and outdoor adventurers alike with its relaxed ambience and local attractions. The community offers access to leisure activities including resort-style amenities and quality golfing experiences at local golf courses. With nearby attractions featuring a theme park, film studio, and a sports facility stadium, this quaint locale provides a delightful retreat with plenty of engaging activities.
  • Lake Buena Vista: Situated 18km from Kissimmee, Lake Buena Vista is a lively city that caters to families, entertainment seekers, and business travellers. The city boasts a variety of activities including expansive shopping areas and bustling shopping mall centres, along with resort-style leisure options. The proximity to major attractions such as a theme park, film studio, and a sports facility stadium makes it an ideal destination for those looking to blend relaxation with a dash of excitement.

Booking with Stayz is simple

Looking to cut costs on your upcoming journey? Having some flexibility with your travel dates can make a difference, as prices often fluctuate. You may also enjoy considerable savings by opting for a longer stay. To find a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday let.

Stayz Trips: Effortless planning

Stayz's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your existing itineraries. You can easily access properties you've saved or booked, now neatly organised into Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The sunny setting of Kissimmee is ready to explore

Take a holiday to Kissimmee and enjoy the area's festivals, entertainment and opera. Renowned for its theme park, shopping and sporting events, this city welcomes all visitors. Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are just a couple of the must-see attractions. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Kissimmee

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Kissimmee a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Hollywood Studios® (10.3 mi / 16.6 km)
  • Disney's Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal’s Volcano Bay (12.4 mi / 19.9 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)

Exploring the natural landscape of Kissimmee

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Kissimmee is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Tohopekaliga (6.1 mi / 9.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)
  • Alligator Lake (13.3 mi / 21.4 km)

Seasonal weather in Kissimmee

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 27°C.

How to get to and around Kissimmee

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.8 mi (2.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Orlando International Airport (MCO), which is 11.4 mi (18.3 km) away.

If you prefer train travel, you can make your way to Kissimmee Station. Utilise the area's public transport and catch a ride on the metro at Tupperware Station or Poinciana Station and easily see more of the city.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a holiday home?
If you're on you way to Kissimmee, Bellavida is one of the most sought-after neighbourhoods to stay. No matter your travel style, Stayz is bound to have a property here that matches your needs.
What is the most popular type of holiday home accommodation in Kissimmee?
The most in-demand types of holiday homes in Kissimmee are houses. Looking for something different? Stayz offers a variety of options to match our guests' needs, so you'll see holiday homes in loads of shapes and sizes. The ideal fit is ready and waiting for you — book yours today.
How much does it cost to rent a holiday home in Kissimmee?
A range of things can determine the price of a holiday home in Kissimmee, including the season, length of stay and type of property. Still, all our holiday homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Kissimmee?
When you travel and the style and size of the property will determine the cost of your beachside holiday home. Enter your Kissimmee travel dates to see your options on Stayz. Can't live without a hot tub? Use our filters to pick the amenities and features you want in your beach house.
Are there pet-friendly holiday homes in Kissimmee?
Yes. You can pick from 14 ,063 holiday homes that allow pets in Kissimmee. Many of our pet-friendly holiday homes come with an area outdoors for your four-legged friend to have fun in, dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect place on Stayz.
Can I rent a house with a pool in Kissimmee?
Tick the "pool" box in our filter tool and select from 13 ,636 houses with private pools in Kissimmee on Stayz. Morning swim, afternoon splash or midnight soak? Leisure time is up to you when your Stayz holiday property comes with its own swimming pool.
What are popular home amenities in Kissimmee?
The most popular home amenities people are searching for in Kissimmee include a nearby river, a barbecue grill and a firepit. Whether you're on the road with family, friends or even pets, Stayz holiday homes have the best amenities for fun and relaxation with the people closest to you.
Are there large group holiday homes in Kissimmee?
With 6 ,071 properties that can host 10 guests or more in Kissimmee, you won't have to keep anyone off the invite list. From family holidays to special events like birthday and Christmas parties, Stayz will help you find a large group home to suit the occasion.
Are there holiday homes in Kissimmee that welcome kids?
With 14 ,021 family-friendly holiday homes to choose from in Kissimmee, now is an awesome time to introduce your children to the joys of travel. Simply click on our "Properties good for families" filter box to look for stays that come with conveniences perfect for holidaying families, like extra bedrooms, swimming pools, bunk beds and entertainment units.
What are the top attractions for families in Kissimmee?
Keep your kids entertained at these leading family-friendly attractions in Kissimmee:

  • Aquatica
  • Discovery Cove
  • Disneys Typhoon Lagoon Water Park

Are there one-bedroom holiday homes in Kissimmee?
You can choose from 319 one-bedroom homes in Kissimmee. Whether you're searching for a secluded cottage or an upmarket condo, our one-bedroom properties are great if you don't require a huge amount of space. One of the best things about having your own digs? You won't have to share your getaway with strangers.
Can I find two-bedroom holiday homes in Kissimmee?
Pick from 889 two-bedroom holiday homes in Kissimmee. Settle the kids into the second room or fill it with a couple of your best buddies. There's a spot for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in Kissimmee?
You'll find 4 ,721 holiday homes with WiFi in Kissimmee. If you'd like to disconnect from the world on your trip, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Kissimmee?
Select your travel dates and then use our filters to view holiday homes with ac in Kissimmee on Stayz. With 13 ,802 air-conditioned properties available here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday home in Kissimmee?
The minimum age allowed can vary across properties on Stayz, so look at the rules of the holiday home in Kissimmee you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Kissimmee for?
The length of time you can rent a holiday home in Kissimmee depends on the property. Simply enter your selected dates to view a list of options offering extended stays. With loads of amenities like air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find a terrific place to call your home away from home in Kissimmee.

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