Compare Vacation Rentals & Airbnb in Kissimmee

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Kissimmee vacation rentals
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20413 Rentals and Airbnb in Kissimmee

Best family friendly Kissimmee vacation rentals

Among the 20413 accommodations in Kissimmee, here are the 4 best family friendly rentals

6 Bed, Pool Home -Pearadise Palms -Gameroom-resort - Kissimmee
9.2 84 reviews

6 Bed, Pool Home -Pearadise Palms -Gameroom-resort

apartment, Kissimmee
This six-bedroom villa, ‘6 Bed, Pool Home - Pearadise Palms - Gameroom-resort’, is located in the Storey Lake Resort community in Kissimmee, Florida, a short distance from Walt Disney World.
The 6-bedroom, 5-bathroom property sleeps up to 16 guests and boasts a private screened pool and Jacuzzi, a games room with ping pong and foosball, and is close to the Storey Lake Resort Clubhouse with its lazy river and water slides.
Spacious 5 Bedroom Private Pool House Near Disney! - Kissimmee
9.6 61 reviews

Spacious 5 Bedroom Private Pool House Near Disney!

apartment, Kissimmee
This five-bedroom, three-bathroom holiday home is located within the Lake Berkley Resort gated community in Kissimmee, Florida, just minutes (approximately 8km) from Walt Disney World.
The property boasts a private pool and jacuzzi, access to resort amenities including a further pool, gym and playground, sleeps up to 13 guests, and features a spacious interior with a games room, large TVs with streaming, and a screened patio.
Family Stay Near Disney - Kissimmee
9.0 2 reviews

Family Stay Near Disney

apartment, Kissimmee
This two-bedroom, two-bathroom Kissimmee apartment, sleeping up to 15 guests, is conveniently located approximately 11-13km from Disney Springs, Gatorland, and Disney's Wide World of Sports.
The self-catering property boasts a fully equipped kitchen, private balcony, swimming pool, Jacuzzi, free Wi-Fi, parking, and in-unit laundry facilities, ensuring a comfortable stay near major theme parks.
Magical Family Home 8min Disneyworld Pool/spa Sleeps 22 - Kissimmee
9.4 148 reviews

Magical Family Home 8min Disneyworld Pool/spa Sleeps 22

house, Kissimmee
This Disney-themed vacation home is located in Kissimmee, just 11 kilometres from Gatorland and a short 8-minute drive from Disney World. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This spacious house sleeps up to 22 guests in 9 bedrooms and 5 bathrooms. Enjoy a private pool, hot tub, a fully equipped kitchen, and a relaxing garden, perfect for unwinding after a day of exploring the theme parks.

Best Kissimmee vacation rentals with parking

Sweet Memories - Kissimmee
9.4 67 reviews

Sweet Memories

house, Kissimmee
Sweet Memories is a holiday home in Kissimmee, just 10 miles from both Gatorland and Disney's Wide World of Sports, making it an ideal base for exploring the area's attractions. The property has received excellent user and location ratings, as well as a very good cleanliness rating.
This seven-bedroom property is perfect for large families or groups of friends. It offers a private pool, a spa bath, a hot tub, a fully equipped kitchen, an indoor play area, an open-air bath, a washing machine, free Wi-Fi and parking.
Casita Disney! Cozy And Boho Townhouse Near Disney - Kissimmee
9.8 109 reviews

Casita Disney! Cozy And Boho Townhouse Near Disney

house, Kissimmee
This three-bedroom, two-bathroom townhouse is situated in a gated community off Highway 192 in Kissimmee, Florida, approximately 32 kilometres from all Walt Disney World Parks and close to shops and restaurants.
The property, sleeping up to six guests, boasts a boho-chic interior, a private balcony, a fully equipped kitchen, resort access including two pools and children's play areas, and toddler-friendly amenities such as a high chair and stroller.
Luxurious Dream 4/3 Bedroom Home W/private Pool - Kissimmee
9.8 295 reviews

Luxurious Dream 4/3 Bedroom Home W/private Pool

house, Kissimmee
This luxurious four-bedroom, three-bathroom property is located in the Le Reve community in Kissimmee, Florida, approximately 9km from Disney Springs and 40km from Orlando International Airport.
The spacious 167sq m two-storey house boasts a private heated pool, a fully equipped kitchen, and access to a community fitness centre; it comfortably sleeps eight guests and includes in-house laundry facilities.
4 Bd 4 Ba Bella Vida 440 Lf - Kissimmee
9.5 151 reviews

4 Bd 4 Ba Bella Vida 440 Lf

house, Kissimmee
This four-bedroom property is located in Kissimmee, just under ten miles from Disney's Hollywood Studios and Disney's Wide World of Sports, making it ideal for families or groups wanting to explore the area's attractions. The house has received excellent ratings for location, cleanliness and overall user experience.
The 177 square metre house offers ample space for a comfortable stay. The property boasts a range of amenities including a swimming pool, spa, fitness centre, and a fully equipped kitchen with a dishwasher, making it perfect for relaxing and entertaining.

Frequently Asked Questions about vacation rentals in Kissimmee

  • What are the top family-friendly attractions in Kissimmee?

    You've got to check out the theme parks, obviously! Walt Disney World Resort is a classic, and Universal Orlando Resort is great for older kids. For something a bit different, head to the Aquatica Orlando water park.
  • What are the best Airbnb and vacation rentals in Kissimmee?

    Modern Luxury Villa In Storey Lake, 2bd/2ba Condo Close To Disney At Storey Lake #96 and Locationnew 4/3 W/pool 10min To Disney-orlando are the most popular Airbnb and vacation rentals in Kissimmee among travelers.

  • What types of vacation rentals can I find in Kissimmee?

    You can find all kinds of vacation rentals in Kissimmee, Florida. There are entire houses, apartments, bungalows and cottages you can rent out, as well as more unique vacation rentals, such as cabins, tree houses, or tiny houses. We can help you find the right vacation rental for your stay in Kissimmee.

  • When is the best time to book a vacation rental in Kissimmee?

    The best time to book is probably in the off-season, from September to November, or January to February. You'll get better deals and avoid the crowds. But remember, school holidays will always be busy.
  • What are the most popular Airbnbs in Kissimmee?

  • What is there to do in Kissimmee?

    Kissimmee is world-famous for its theme parks, like Walt Disney World Resorts, Seaworld Parks & Resorts, and Universal Orlando Resort. However, there is much more to Kissimmee than theme parks. You can get out in nature, go fishing, ride a hot air balloon, go on an airboat adventure through the Central Florida Everglades, visit a Native American Village, go horse riding and more. You can also catch a game with the Orlando Solar Bears or get a round of golf in. There is something for everyone in Kissimmee.

  • What are the best budget-friendly activities in Kissimmee?

    You can always visit the Kissimmee Lakefront Park for a picnic or a walk around the lake. Or, if you're feeling adventurous, try the Boggy Creek Airboat Rides for a fun day out.
  • What are the best vacation rentals with a pool in Kissimmee?

  • What are the main attractions in Kissimmee?

    Top attractions in Kissimmee include Old Town, where you'll find a Ferris wheel, ride attractions like a roller coaster, a classic merry-go-round and more. You can visit Old Town for free anytime, and there are many places to eat and drink. Medieval Times Dinner and Tournament is another popular attraction, where you're welcomed into the king's court for a four-course feast and a show complete with jousting and more. Then, of course, there's Walt Disney World, which needs no introduction.

  • What are the best restaurants with local dishes in Kissimmee?

    There's a great place called The Dixie Crossroads, known for their seafood. For something a bit more casual, try The Boathouse for their fresh fish and views of the lake. And you can't go wrong with The Old Town Restaurant, a local favourite.
  • What are the best rentals for families and kids in Kissimmee?

  • How can I get around Kissimmee?

    It's easy to get around Kissimmee, as you'll find a range of transportation options, from taxis and rideshares like Uber and Lyft to shuttles and LYNX, the public transportation system for Central Florida mostly consisting of local bus services.

  • What are the best walking or cycling routes in Kissimmee?

    The Shingle Creek Trail is a great option for a leisurely walk or bike ride. It's a paved trail that runs along the creek, and it's a great place to spot wildlife. The East Tohopekaliga Trail is another good choice, offering scenic views of the lake.
  • What are the best rentals or Airbnbs with a jacuzzi in Kissimmee?

  • When is the best time to go to Kissimmee?

    The best time to come to Kissimmee is between January and April, as there is little rain and the temperatures are warm, but not too hot.

  • Are there pet-friendly attractions in Kissimmee?

    Yes, there are! The Kissimmee Lakefront Park is pet-friendly, and you can often see people walking their dogs around the lake. The Celebration Town Center is also a good option, with plenty of shops and restaurants that welcome furry friends.
  • What are the benefits of choosing a vacation rental in Kissimmee?

    Vacation rentals offer more space and privacy than a hotel, and they often come with amenities like a kitchen and laundry facilities. They're also a great option for families or groups of friends travelling together.
  • What are the top sports attractions and facilities in Kissimmee?

    For sports fans, there's the Silver Spurs Arena, which hosts rodeo events and concerts. You can also find golf courses like the Kissimmee Bay Country Club and the Celebration Golf Club.

Popular destinations

Best Kissimmee vacation rentals with a balcony

Beautiful Lake View Golf Home 2723 - Kissimmee
9.5 104 reviews

Beautiful Lake View Golf Home 2723

apartment, Kissimmee
This four-bedroom holiday home is located near a lake in Kissimmee, just a short distance from Remington Golf Club, Osceola Center for the Arts, and Osceola Flea and Farmers Market. Guests have consistently rated this property as excellent for its location, cleanliness, and overall experience.
The property comfortably accommodates up to eight guests and features a fully equipped kitchen, four bathrooms, and a dining area. Enjoy the private pool, terrace, and stunning lake views, or explore nearby golf courses, attractions, and local markets.
House ∙ 4 Bedrooms ∙ 11 Guests - Kissimmee
No reviews

House ∙ 4 Bedrooms ∙ 11 Guests

house, Kissimmee
This family-friendly holiday home in Kissimmee is located on a corner lot within a gated community, offering easy access to major Orlando theme parks such as Animal Kingdom and Magic Kingdom, all within a 20-minute drive.
This spacious villa accommodates up to 11 guests with 4 bedrooms and 3 bathrooms, featuring a private heated swimming pool, an air-conditioned Glow in the Dark Kids Game Room, mini golf, Xbox, air hockey, foosball, and complimentary amenities including toiletries, linens, and towels.
3830 Premier Villa 6bd Private Pool And Game Room - Kissimmee
9.2 111 reviews

3830 Premier Villa 6bd Private Pool And Game Room

house, Kissimmee
This six-bedroom property is situated in the Sonoma Resort at Tapestry, just a short drive from popular attractions like Gatorland and SeaWorld. The house has received excellent ratings for its location, cleanliness, and overall user experience.
This spacious villa offers 314 square metres of living space, ideal for large families or groups. Guests can enjoy a private pool, spa, fitness centre, and a range of other amenities, including a garden, terrace, and balcony.
Lakeview 6-bedroom Retreat With Game Room, Private Pool, Spa & Resort Amenities - Ideal For Families & Groups - Kissimmee
9.7 173 reviews

Lakeview 6-bedroom Retreat With Game Room, Private Pool, Spa & Resort Amenities - Ideal For Families & Groups

house, Kissimmee
This Kissimmee property is located just 12.4 kilometres from Gatorland and 16 kilometres from both Disney Springs and Disney's Wide World of Sports, making it a great choice for families visiting the area. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This five-bedroom, seven-bathroom home offers spacious accommodation for large groups. Guests can enjoy a private pool, a fully equipped kitchen, a fitness centre, and a range of other amenities, including a sauna, spa, and tennis court.

Best Kissimmee vacation rentals with air conditioning

Charming 3 Bed Villa At Seven Dwarfs - Kissimmee
9.8 39 reviews

Charming 3 Bed Villa At Seven Dwarfs

apartment, Kissimmee
This three-bedroom, two-bathroom villa is situated in the Villas of the Seven Dwarfs community in Kissimmee, Florida, approximately 13 kilometres from Walt Disney World's Magic Kingdom.
The 6-guest property boasts a fully equipped kitchen with granite worktops, a private swimming pool and Jacuzzi, plus access to on-site amenities including a fitness centre and games room, all within a 24-hour security gated resort.
Spacious 3 Bedroom 5 Beds 2.5 Bath 20 Min To Parks - Kissimmee
9.8 13 reviews

Spacious 3 Bedroom 5 Beds 2.5 Bath 20 Min To Parks

apartment, Kissimmee
This three-bedroom, two-bathroom Kissimmee townhouse, located approximately 32km from Walt Disney World Resort and 48km from Universal Orlando Resort, offers a convenient base for exploring central Florida's theme parks.
Sleeping seven guests, this family-friendly property boasts a fully equipped kitchen, swimming pool, fitness centre, and excellent guest reviews, all within a pleasant, tree-lined neighbourhood with easy access to local amenities.
Luxury • Modern • Close2disney • 3bed • 2bath - Kissimmee
9.6 354 reviews

Luxury • Modern • Close2disney • 3bed • 2bath

apartment, Kissimmee
This Kissimmee condo is ideally situated approximately 11-13km from Disney's Hollywood Studios and Disney Springs.
Offering three bedrooms, two bathrooms, a fully equipped kitchen, and access to a swimming pool, Jacuzzi, tennis court, and fitness centre, this spacious property comfortably sleeps a family or group, with free Wi-Fi and parking included.
Why Book A Hotel When You Can Have A Whole Condo ! - Kissimmee
9.9 85 reviews

Why Book A Hotel When You Can Have A Whole Condo !

apartment, Kissimmee
This family-friendly apartment is situated in Venetian Bay Villages, just 1.6 kilometres from Shingle Creek Regional Park and the 192 Flea Market, with other attractions like Give Kids the World Village and Kissimmee Go-Karts within a 5-kilometre radius. It has excellent user, location, and cleanliness ratings, promising a comfortable and enjoyable stay.
The apartment offers 120 square metres of space, accommodating up to 8 guests in its three bedrooms and two bathrooms. It includes a fully equipped kitchen, a washing machine, free Wi-Fi, a TV, a swimming pool, a jacuzzi, a fitness centre, parking, and a family-friendly atmosphere with an arcade/game room.
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