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Kissimmee, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Kissimmee, FL

Compare Vacation Rentals for Families in Kissimmee, FL

Booking a family-oriented vacation rental in Kissimmee, FL keeps you close to top city attractions for a stress-free getaway.

4 Bedroom 3 Bathroom Villas At Seven Dwarfs 8-108 - Kissimmee, FL
8.6 7 reviews
Kissimmee, FL
07/02 – 07/05
$279/nighttotal: $837 (3 )

4 Bedroom 3 Bathroom Villas At Seven Dwarfs 8-108

4 2
house , Kissimmee
This Kissimmee villa is conveniently located 7.1 miles from Disney Springs and Gatorland, and 7.2 miles from Disney's Wide World of Sports Complex.
This 1,470-square-foot vacation home boasts four bedrooms, three bathrooms, and accommodates up to 15 guests, featuring a private pool, fitness center, and on-site mini-market.
All New Renovated 3/2 Condo Close To Parks - Kissimmee, FL
9.8 298 reviews
Kissimmee, FL
07/07 – 07/12
$172/nighttotal: $860 (5 )

All New Renovated 3/2 Condo Close To Parks

3 2
apartment , Kissimmee
This Kissimmee vacation rental is situated in a villa community, just a short walk from parks, shops, and entertainment options. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom apartment comfortably accommodates up to six guests, offering a spacious and relaxing retreat. Enjoy amenities like a private balcony, a swimming pool, and a fitness center, making your stay both comfortable and enjoyable.
Laoxury 3bd Townhome Pool Front In Brilliant Kissimmee - Kissimmee, FL
9.8 8 reviews
Kissimmee, FL
08/14 – 08/16
$212/nighttotal: $424 (2 )

Laoxury 3bd Townhome Pool Front In Brilliant Kissimmee

3 2
apartment , Kissimmee
This 3-bedroom townhome in Kissimmee is located a short walk from the community pool and within 5 miles of Walt Disney World Resort, Disney's Hollywood Studios, Epcot, and Disney's Typhoon Lagoon Water Park, with Old Town and Disney Springs also nearby.
This family-friendly rental sleeps up to 6 guests and features air conditioning, a full kitchen with a dishwasher, and parking, offering a comfortable base for exploring local attractions.
Amazing Disney Resort Style & Free Waterpark 2481 - Kissimmee, FL
9.6 99 reviews
Kissimmee, FL
07/24 – 07/26
$371/nighttotal: $742 (2 )

Amazing Disney Resort Style & Free Waterpark 2481

1 6
house , Kissimmee
This four-bedroom Story Lake Resort townhouse, part of the Amazing Disney Resort Style & Free Waterpark 2481 offer, is located in a newer section of Kissimmee, Florida, minutes from Disney World theme parks.
The property boasts a private pool, Mickey Mouse-themed bedroom, sleeps up to 10 guests, and includes access to Story Lake Resort amenities such as water slides, a lazy river, and a fitness center.

Best Kissimmee, FL vacation rentals with parking

10 Mi To Disney World: Townhome W/ Community Pool! - Kissimmee, FL
Kissimmee, FL
06/26 – 06/28
$266/nighttotal: $532 (2 )

10 Mi To Disney World: Townhome W/ Community Pool!

3 6
house , Kissimmee
This Kissimmee vacation home is situated approximately 10 miles from Walt Disney World attractions including Hollywood Studios and Disney Springs, and 9.4 miles from Gatorland.
This 1500 square foot, 3-bedroom townhome accommodates up to 11 guests and features a full kitchen, air conditioning, a community pool, and on-site parking.
Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #57267 - Kissimmee, FL
9.6 14 reviews
Kissimmee, FL
07/13 – 07/17
$488/nighttotal: $1952 (4 )

Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #57267

6 15
house , Kissimmee
Storey Lake Resort 727, a premium Kissimmee villa, is located steps from Shingle Creek Regional Park and within 3 miles of attractions like Capone's Dinner Show and Kissimmee Go-Karts.
This six-bedroom, five-bathroom vacation home features a private pool, game room, fully equipped kitchen, and is perfect for large families or groups seeking a relaxing stay near Disney, with easy access to local attractions and outdoor recreation.
Sonoma Resort7 Bedroom Vacation Home 2606ya - Kissimmee, FL
8.5 267 reviews
Kissimmee, FL
10/14 – 10/18
$358/nighttotal: $1432 (4 )

Sonoma Resort7 Bedroom Vacation Home 2606ya

7 11
house , Kissimmee
Holiday Home L'Etang is located in Corbon, a charming village just 13 miles from the Basilica of Lisieux and Cabourg Racecourse. This house has received very good ratings for user experience, location, and cleanliness.
The home features a modern kitchenette with a dishwasher and oven, a washing machine, and free Wi-Fi. Guests can enjoy a peaceful setting, a private garden, private parking, a swimming pool, a jacuzzi, a terrace, a sauna, a spa, a fitness center, and a tennis court.
4200 Paragraph Drive - Kissimmee, FL
9.3 73 reviews
Kissimmee, FL
11/07 – 11/17
$245/nighttotal: $2450 (10 )

4200 Paragraph Drive

1 10
house , Kissimmee
This Kissimmee vacation home is conveniently located near major attractions, approximately 8 miles from Gatorland and Disney Springs, and 8.5 miles from Disney's Wide World of Sports.
This 2,160-square-foot property boasts a private pool, Jacuzzi, and on-site playground, along with a fully equipped kitchen, free Wi-Fi, and in-house amenities including a washer, dryer, and air conditioning.

Frequently Asked Questions about vacation rentals in Kissimmee, FL

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

    Kissimmee is a great place for families! You'll find a ton of family-friendly attractions here, like the theme parks, of course, but also places like Gatorland, which is a fun and educational experience where you can see alligators up close. Another great option is the Legoland Florida Resort, which is perfect for younger kids. And don't forget about the Aquatica Orlando, a water park with a variety of rides and attractions for all ages.
  • What are the best Airbnb and vacation rentals in Kissimmee, FL?

    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, FL among travelers.

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

    Kissimmee offers top family-friendly attractions like Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando, which provide endless entertainment and fun for families.
  • What are the best restaurants with local dishes in Kissimmee?

    You can find some great local restaurants in Kissimmee. One of my favorites is the Pecos Bill Tall Tale Inn and Cafe, which is a classic Western-themed restaurant with delicious food. Another great option is the Bob Evans, which is a popular chain restaurant with a variety of American dishes. And if you're looking for something a little more upscale, you can check out the Flemings Prime Steakhouse & Wine Bar, which is a great place to enjoy a special meal.
  • What are the most popular Airbnbs in Kissimmee, FL?

  • What are the best modes of transportation for families in Kissimmee, FL?

    The best modes of transportation for families in Kissimmee include renting a car, using rideshare services like Uber or Lyft, or taking advantage of shuttle services provided by theme parks and resorts.
  • What are the best walking or cycling routes in Kissimmee?

    Kissimmee has some great walking and cycling routes. One of my favorites is the Shingle Creek Trail, which is a paved trail that runs along the Shingle Creek. You can also check out the East Tohopekaliga Trail, which is a scenic trail that runs through the heart of Kissimmee. And if you're looking for a more challenging ride, you can try the West Tohopekaliga Trail, which is a longer and more challenging trail that winds through the countryside.
  • What are the best vacation rentals with a pool in Kissimmee, FL?

  • Which restaurants in Kissimmee, FL are the most family-friendly?

    Some family-friendly restaurants in Kissimmee include Sweet Tomatoes, Texas Roadhouse, and Celebration Town Tavern, which offer a welcoming atmosphere and menus suitable for all ages.
  • Are there pet-friendly attractions in Kissimmee?

    Yes, there are a few pet-friendly attractions in Kissimmee. You can bring your furry friend to the Kissimmee Lakefront Park, which has a dog park. You can also check out the Celebration Town Center, which is a pet-friendly area with shops and restaurants. And if you're looking for a place to stay with your pet, there are a number of pet-friendly hotels and vacation rentals in the area.
  • What are the best rentals for families and kids in Kissimmee, FL?

  • Are there any family-friendly outdoor activities in Kissimmee, FL?

    Yes, families can enjoy outdoor activities like visiting Kissimmee Lakefront Park, exploring Gatorland, or taking an airboat ride in the Everglades, providing exciting experiences and opportunities to connect with nature.
  • What are the best rentals or Airbnbs with a jacuzzi in Kissimmee, FL?

  • Which historical sites in Kissimmee, FL are suitable for children?

    Historical sites like the Pioneer Village at Shingle Creek, the Osceola County Welcome Center and History Museum, and the Kissimmee Historic District offer educational experiences suitable for children, showcasing the region's history and heritage.
  • What cultural experiences in Kissimmee, FL can families enjoy together?

    Families can enjoy cultural experiences in Kissimmee by attending events at the Osceola Arts, exploring the exhibits at the Museum of Military History, or visiting the Osceola County Fair, which showcases local traditions and culture.
  • Where can families find local cuisine in Kissimmee, FL?

    Families can find local cuisine at places like the Kissimmee Farmers Market, Old Town Kissimmee, or local restaurants that offer regional dishes, providing a taste of the local flavors.
  • Are there areas of Kissimmee, FL to avoid with young children?

    While Kissimmee is generally safe for families, it's advisable to exercise caution and avoid isolated areas or neighborhoods that may not be well-lit or frequented by tourists, especially at night.
  • Are there any special events or festivals in Kissimmee, FL that families can attend?

    Families can attend special events and festivals in Kissimmee like the Osceola County Fair, the Festival of Rides, or the Old Town Classic Car Show, which offer family-friendly entertainment and activities.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Kissimmee, FL

Enjoy stunning views from your private terrace when you book one of these vacation rentals in Kissimmee, FL.

Cozy 4br Family Villa | Community Amenities- Pool & Playground - Kissimmee, FL
10 1 review
Kissimmee, FL
07/22 – 08/02
$175/nighttotal: $1925 (11 )

Cozy 4br Family Villa | Community Amenities- Pool & Playground

4 7
apartment , Kissimmee
Your Orlando Escape - Gated Resort With Amenities! is located in the Venetian Bay Villages community in Kissimmee, Florida, 15 minutes from Walt Disney World, 20 minutes from Universal Studios and SeaWorld, and 5 minutes from shopping and dining on US-192.
This pet-friendly townhome boasts 1,470 square feet, four bedrooms, 3.5 bathrooms, and accommodates up to 10 guests, featuring a ground-floor primary suite, resort-style amenities including multiple pools and a fitness center, and convenient access to major theme parks.
Lake View/spa/game Room/storey Lake 22102 - Kissimmee, FL
9.2 57 reviews
Kissimmee, FL
07/13 – 07/17
$728/nighttotal: $2912 (4 )

Lake View/spa/game Room/storey Lake 22102

9 15
house , Kissimmee
This nine-bedroom, five-bathroom vacation home in Kissimmee offers convenient access to Shingle Creek Regional Park, Kissimmee Go-Karts, and the 192 Flea Market, all within three miles.
The property boasts a private pool, hot tub, game room, fully equipped kitchen, laundry facilities, and a fitness center, comfortably accommodating large families or groups.
Sunny South Facing Pool With Hot Tub And Lake View Near Disney - Kissimmee, FL
9.5 63 reviews
Kissimmee, FL
11/07 – 11/17
$316/nighttotal: $3160 (10 )

Sunny South Facing Pool With Hot Tub And Lake View Near Disney

1 10
house , Kissimmee
This Kissimmee vacation home is ideally situated near major attractions, approximately 7.6 miles from Gatorland, 8.9 miles from Disney's Wide World of Sports Complex, and 9.1 miles from Disney's Hollywood Studios.
This 2,500-square-foot villa boasts six bedrooms, three bathrooms, a private pool, spa, and fitness center, comfortably accommodating large families or groups and offering numerous on-site amenities.
Venetian Bay Villa 4 Bedroom Townhouse - Near Disney - Kissimmee, FL
9.7 3 reviews
Kissimmee, FL
07/20 – 07/29
$185/nighttotal: $1665 (9 )

Venetian Bay Villa 4 Bedroom Townhouse - Near Disney

4 7
house , Kissimmee
Venetian Bay Villa is a 4-bedroom townhouse located in a quiet Kissimmee neighborhood, 5.2 miles from Gatorland, 10 miles from Disney Springs, and 10 miles from Disney's Wide World of Sports. It has excellent user and location ratings.
The townhouse has a floor area of 1470 square feet and can accommodate up to 10 guests. It features a fully equipped kitchen, 4 bedrooms, 3 bathrooms, a private outdoor space with a patio and terrace, and access to amenities such as a hot tub, fitness room, outdoor swimming pool, fishing, hiking, and barbecue facilities.

Best Kissimmee, FL vacation rentals with air conditioning

25 Minutes To Disney World! Family-sized Townhouse - Kissimmee, FL
9.6 126 reviews
Kissimmee, FL
07/22 – 08/02
$144/nighttotal: $1584 (11 )

25 Minutes To Disney World! Family-sized Townhouse

4 7
apartment , Kissimmee
This Kissimmee vacation home is located in the Venetian Bay Villages community, less than a mile from Shingle Creek Regional Park and within three miles of Give Kids the World Village and Kissimmee Go-Karts.
This 1,470-square-foot house features four bedrooms, three bathrooms, and accommodates eight guests, offering a private pool, a fully equipped kitchen, free Wi-Fi, and access to a shared water park and fitness center.
Amazing House! 2794 @ Storey Lake 9 Bed/5 Bath - Kissimmee, FL
9.6 73 reviews
Kissimmee, FL
07/10 – 07/24
$441/nighttotal: $6174 (14 )

Amazing House! 2794 @ Storey Lake 9 Bed/5 Bath

1 15
house , Kissimmee
This luxury home is located in the Storey Lake resort in Kissimmee, offering convenient access to major attractions, shopping, and dining.
This 9-bedroom, 5-bathroom house accommodates up to 16 guests and features a kitchen, air conditioning, swimming pool, jacuzzi, garden, and a BBQ grill, with pool and whirlpool spa warming available for an additional fee.
9 Mi To Disney: Resort Getaway W/ Private Patio! - Kissimmee, FL
10 3 reviews
Kissimmee, FL
09/18 – 09/20
$262/nighttotal: $524 (2 )

9 Mi To Disney: Resort Getaway W/ Private Patio!

3 8
house , Kissimmee
This Kissimmee vacation home boasts a prime location, approximately 7.6 miles from Gatorland, 8.7 miles from Disney's Wide World of Sports, and 9 miles from Disney's Hollywood Studios.
This 1,290-square-foot property features three bedrooms, sleeps up to 15 guests, and includes a private pool, jacuzzi, and fully equipped kitchen with a dishwasher; on-site parking is also available.
No Airbnb Fee! Harry Potter Room Pool In Resort - Kissimmee, FL
9.3 188 reviews
Kissimmee, FL
10/10 – 10/17
$130/nighttotal: $910 (7 )

No Airbnb Fee! Harry Potter Room Pool In Resort

1 3
house , Kissimmee
This Kissimmee vacation home boasts a central location, approximately 7 miles from Walt Disney World, 14 miles from Universal Studios Florida, and 10 miles from SeaWorld, offering easy access to major theme parks and attractions.
This four-bedroom, three-bathroom house sleeps eight guests and features a private pool, themed children's rooms (Harry Potter and Minions), free parking for two cars, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher; a $25 one-time access card fee applies for the gated community.
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