Kissimmee holiday homes

We found 32,016 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Kissimmee by choosing from 1624 houses, 67 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:4 Dec - 11 Dec

Room
Pool
Dining
Exterior
Exceptional
(127 reviews)

Access to 3 Private GOLF COURSES+Waterpark+POOL & SPA+Gameroom+THEATER+Disney

Kissimmee

7% off
NZ$17,863
for 7 nights, 1 home
NZ$2,552 per night
includes taxes & fees
Access to 3 Private GOLF COURSES+Waterpark+POOL & SPA+Gameroom+THEATER+Disney
Open concept floor
Lazy river, splash zone
Resort aerial
Fully equipped kitchen
Exceptional
(17 reviews)

"Escape to Paradise: Luxurious Vacation Home in Davenport, Florida"

Davenport

7% off
NZ$3,621
for 7 nights, 1 villa
NZ$517 per night
includes taxes & fees
"Escape to Paradise: Luxurious Vacation Home in Davenport, Florida"
Welcome home
Pool
main floor king suite
Kitchen with eating bar
Very good
(47 reviews)

VB009 Venetian Bay Wonders

Kissimmee

9% off
NZ$1,600
for 7 nights, 1 home
NZ$229 per night
includes taxes & fees
VB009 Venetian Bay Wonders
Interior
Exterior
Interior
Room
Exceptional
(20 reviews)

LUXURIOUS 7-Bedroom Villa in Champions Gate , Heated Pool & Resort Access

Davenport

8% off
NZ$6,562
for 7 nights, 1 home
NZ$937 per night
includes taxes & fees
LUXURIOUS 7-Bedroom Villa in Champions Gate , Heated Pool & Resort Access
Private kitchen
Exterior
Interior
Living area
Wonderful
(14 reviews)

Brand new cozy home at Sonoma Resort at Tapestry

Kissimmee

7% off
NZ$4,006
for 7 nights, 1 home
NZ$572 per night
includes taxes & fees
Brand new cozy home at Sonoma Resort at Tapestry
Mediterranean styled villa: you enjoy the entire home - no sharing with other vacationers
Club House Foyer
Club House Patio
Property grounds
Very good
(31 reviews)

Renovated 4BR Villa with Private Pool Spa in Bellavida Resort Near Disney

Kissimmee

5% off
NZ$3,122
for 7 nights, 1 villa
NZ$446 per night
includes taxes & fees
Renovated 4BR Villa with Private Pool Spa in Bellavida Resort Near Disney
Private kitchen
Interior
Exterior
Living area
Very good
(6 reviews)

Big-Bright and Beautiful 6 bedroom home on Emerald Island Resort

Kissimmee

7% off
NZ$2,748
for 7 nights, 1 home
NZ$393 per night
includes taxes & fees
Big-Bright and Beautiful 6 bedroom home on Emerald Island Resort
Pool Patio
Living Room
Dining Room
Kitchen
Excellent
(16 reviews)

CHARMING VILLA AT SONOMA RESORT AT TAPESTRY

Kissimmee

7% off
NZ$4,167
for 7 nights, 1 villa
NZ$595 per night
includes taxes & fees
CHARMING VILLA AT SONOMA RESORT AT TAPESTRY
Exterior
Pool
Interior
Room
Wonderful
(24 reviews)

Magical charm couple miles away from Disney

Kissimmee

7% off
NZ$2,753
for 7 nights, 1 home
NZ$393 per night
includes taxes & fees
Magical charm couple miles away from Disney
Living area
Pool
Interior
Interior
Wonderful
(28 reviews)

SPECIAL! Get UP TO 20% off Weekly Rental with complementary Pool & Spa Heating!

Davenport

7% off
NZ$5,521
for 7 nights, 1 villa
NZ$789 per night
includes taxes & fees
SPECIAL! Get UP TO 20% off Weekly Rental with complementary Pool & Spa Heating!
Terrace/patio
Private kitchen
Living area
Pool
Very good
(6 reviews)

Modern Orlando Retreat – Minutes to Disney, Universal & All the Magic!”

Orlando

8% off
NZ$2,645
for 7 nights, 1 home
NZ$378 per night
includes taxes & fees
Modern Orlando Retreat – Minutes to Disney, Universal & All the Magic!”
Garage-turned-games-room with air hockey, foosball, game consoles and more!
Luxury Patio with Private Pool and Hot Tub, Games, Smart TVs, BBQ and more.
Large Capacity Living Area with 3 Big Screen TVs
Private Movie Theatre with giant projection screen and cinema style recliners
Excellent
(15 reviews)

Upstay Family Resort Mansion- Pool, Games, Theater

Kissimmee

7% off
NZ$9,679
for 7 nights, 1 home
NZ$1,383 per night
includes taxes & fees
Upstay Family Resort Mansion- Pool, Games, Theater
Upstairs Lounge with Air Hockey Game
Private Swimming Pool and Hot Tub
Spacious Group Friendly Design
Large Capacity Dining Table
Very good
(14 reviews)

Upstay: Luxury 10BR Mansion w Pool,Hot Tub & Games

Kissimmee

7% off
NZ$5,530
for 7 nights, 1 home
NZ$790 per night
includes taxes & fees
Upstay: Luxury 10BR Mansion w Pool,Hot Tub & Games
Property grounds
Pool
Exterior
Private kitchen
Wonderful
(40 reviews)

6-Bed Villa, Private Pool & Hot Tub! Game Room | Gated Resort near Disney

Kissimmee

5% off
NZ$3,648
for 7 nights, 1 home
NZ$521 per night
includes taxes & fees
6-Bed Villa, Private Pool & Hot Tub! Game Room | Gated Resort near Disney
Dining
Pool
Private kitchen
Living area
Wonderful
(158 reviews)

Charming Home Perfect for Families! 3/3 with Pool

Davenport

7% off
NZ$2,067
for 7 nights, 1 home
NZ$295 per night
includes taxes & fees
Charming Home Perfect for Families! 3/3 with Pool
Dining
Community clubhouse
Private kitchen
Room
Exceptional
(94 reviews)

Flash Sale - Themed 9BR New Home@Disney, Home Theater, Private Pool/SPA, Game Rm

Kissimmee

7% off
NZ$5,551
for 7 nights, 1 home
NZ$793 per night
includes taxes & fees
Flash Sale - Themed 9BR New Home@Disney, Home Theater, Private Pool/SPA, Game Rm
Dining
Exterior
Private kitchen
Pool
Wonderful
(19 reviews)

New Lovely Home in Sonoma Resort at Tapestry

Kissimmee

7% off
NZ$4,045
for 7 nights, 1 home
NZ$578 per night
includes taxes & fees
New Lovely Home in Sonoma Resort at Tapestry
Spacious Open Concept Design
Private Swimming Pool
Garage-turned-games-room with Mario Bros theme
In-home Movie Theatre with Disney-themed Decorations
Wonderful
(20 reviews)

Upstay: 15BR Villa w Games Room, Pool & Cinema

Kissimmee

7% off
NZ$9,289
for 7 nights, 1 home
NZ$1,327 per night
includes taxes & fees
Upstay: 15BR Villa w Games Room, Pool & Cinema
open floor plan
the cluhouse deck overlooks a lake.
Corner unit, facing reserve and close to small pool and playground
3 small pools
Wonderful
(76 reviews)

VB006 Affordable Venetian Bay Townhouse With Room For Ten

Kissimmee

9% off
NZ$1,605
for 7 nights, 1 villa
NZ$229 per night
includes taxes & fees
VB006 Affordable Venetian Bay Townhouse With Room For Ten
Large Capacity Dining Table
Private Pool and Hot Tub
Luxurious Bedroom With A King Bed Featuring Vibrant Wall Art And A Smart TV
In-Home Games Room with Putt-Putt Golf and More
Excellent
(13 reviews)

Upstay: Themed Family Home w Pool & Games Room

Kissimmee

7% off
NZ$6,247
for 7 nights, 1 home
NZ$892 per night
includes taxes & fees
Upstay: Themed Family Home w Pool & Games Room
Upstairs TV Lounge
Private Sundeck with Swimming Pool
Comfortable Furnishings
Indoor Family Dining Area
Very good
(35 reviews)

Family Home with Pool, BBQ & Cinema Near Disney

Kissimmee

7% off
NZ$3,436
for 7 nights, 1 home
NZ$491 per night
includes taxes & fees
Family Home with Pool, BBQ & Cinema Near Disney
Poolside Dining Area with BBQ Grill
Private Swimming Pool and Spill Over Hot Tub Jacuzzi
Spacious Open Concept Design
In House Games Room with Air Hockey, Foosball and Pool Table
Very good
(24 reviews)

Garden View 6BR Escape with Pool, Hot Tub & Games

Kissimmee

7% off
NZ$3,877
for 7 nights, 1 home
NZ$554 per night
includes taxes & fees
Garden View 6BR Escape with Pool, Hot Tub & Games
Expansive Living Room with Smart TV and High Speed WiFi
Large Swimming Pool, Hot Tub and Private Garden Facing Sundeck
In House Movie Theatre
Fun Games Room with Foosball, Table Tennis and Pool
Excellent
(19 reviews)

Upstay—Vibrant Home w Themed Rooms, Pool & Games

Kissimmee

7% off
NZ$3,458
for 7 nights, 1 home
NZ$494 per night
includes taxes & fees
Upstay—Vibrant Home w Themed Rooms, Pool & Games
free wifi, extended cable and long distance within Canada and USA
Welcome Home
fully equipped kitchen
open plan main floor
Wonderful
(36 reviews)

VB043 4 Bedroom, 3 Bath Townhouse

Kissimmee

9% off
NZ$1,605
for 7 nights, 1 home
NZ$229 per night
includes taxes & fees
VB043 4 Bedroom, 3 Bath Townhouse
  • Peace of mind

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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 fun: Enjoy theme parks, amusement attractions and outdoor adventures that cater to all ages.
  • Scenic natural beauty: Explore beautiful lakes and parks that offer a breath of fresh air for outdoor enthusiasts.
  • Cultural vibes: Experience local cultural events and warm community spirit.
  • Sunny holidays: Bask in endless sunny days and relaxed, welcoming ambience.
  • Versatile experiences: Ideal for both romantic escapes and family getaways, delivering memorable moments.

Top attractions in and around Kissimmee

Kissimmee, Florida is a vibrant city offering a mix of family-friendly fun and cultural experiences. Visitors can explore exciting theme parks, scenic lakes, and amusement parks, all within a welcoming atmosphere. Whether you’re in the mood for outdoor adventures or a bit of local culture, Kissimmee provides a memorable escape for families, entertainment enthusiasts, and business travellers alike.

  • Osceola Heritage Park: Enjoy a family-friendly urban park with city charm and outdoor vibes, perfect for a leisurely day in Kissimmee.
  • Universal Studios Florida: Experience thrilling entertainment and family fun at this theme park, located 21km away.
  • Lake Cecile: Revel in the scenic, beach-like ambience and romantic outdoor setting of this Kissimmee lake.

Things to do recommended for couples

Kissimmee offers enchanting experiences for couples, from a scenic hot air balloon ride at dawn to a sunset dinner cruise on Lake Tohopekaliga. Stroll hand-in-hand through the lush gardens of the Leu Gardens or explore the charming streets of Old Town for a delightful evening together.

Things to do recommended for families

Families visiting Kissimmee can experience the thrilling rides at Disney World and the enchanting wildlife at Gatorland. Enjoy a fun-filled day at Old Town, where kids can ride vintage attractions and indulge in delicious treats.

Things to do recommended for groups

Groups visiting Kissimmee can experience the thrill of the theme parks, enjoy a scenic airboat ride through the Everglades, and explore the vibrant local markets for unique souvenirs and tasty treats.

*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

If you're heading off on a trip with a group, your family, your pets, or planning an extended stay, be sure to use the appropriate filters to reflect your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Kissimmee with young kids: Traveling with little ones can be challenging. You need to ensure their comfort and safety, as well as access to age-appropriate amenities, such as a private swimming pool. It’s also wise to consider your closeness to family-friendly attractions.
  • Taking your pets with you to Kissimmee: For many families, a getaway isn’t truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Kissimmee: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Kissimmee

Kissimmee, Florida offers a fantastic family holiday with endless sunny days and friendly vibes. Enjoy spacious retreats, explore local attractions, and experience a warm, business-friendly atmosphere. It's a perfect blend of family fun and romantic excursions, all just miles from the magic of Disney. Discover a city that truly caters to diverse interests, making every holiday experience memorable.

  • Orlando: Orlando is a lively metropolis with Kissimmee nestled within its expanse. With its mixed appeal for family, entertainment, and business pursuits, travellers enjoy a dynamic blend of experiences. The area boasts a variety of resorts, expansive shopping areas, and a well-regarded arts centre. Renowned for its proximity to world-class theme parks, film studios, and even nearby beaches, Orlando offers an enticing mix of urban excitement and leisure.
  • Four Corners: Four Corners presents a charming village atmosphere in the Kissimmee area. It caters to families, entertainment seekers, and those with a taste for outdoor adventures. Visitors can explore local resorts, enjoy a round of golf at scenic courses, and take in the unique setting of a village life. Nearby attractions include theme parks, film studios, and a prominent sports facility stadium, making it a diverse destination for a day out.
  • Lake Buena Vista: Located 18km from Kissimmee, Lake Buena Vista is a vibrant city known for its family-friendly, entertainment-focused, and business-oriented appeal. The area features numerous resorts, bustling shopping areas, and a central shopping mall. With theme parks, film studios, and a notable sports facility stadium in the vicinity, Lake Buena Vista promises a well-rounded travel experience filled with both excitement and relaxation.

Booking with Vrbo is a breeze

Looking to cut costs on your next journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a convenient platform to plan new journeys, refine your existing arrangements, or manage your bookings. The properties you’ve saved or reserved are neatly organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, head over to: https://www.bookabach.co.nz/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 Cecile (4.9 mi / 8 km)
  • Lake Tohopekaliga (6.1 mi / 9.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Little Lake Bryan (8.1 mi / 13.1 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, Bookabach 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? Bookabach 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 Bookabach. 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 Bookabach.
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 Bookabach. Morning swim, afternoon splash or midnight soak? Leisure time is up to you when your Bookabach 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, Bookabach 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, Bookabach 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 Bookabach.
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 Bookabach. 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 Bookabach, 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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