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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.

Modern 3br 2.5bth Terra Verde Home With Hot Tub! - Kissimmee, FL
9.5 17 reviews
Kissimmee, FL
08/10 – 08/24
$118/nighttotal: $1652 (14 )

Modern 3br 2.5bth Terra Verde Home With Hot Tub!

1 2
house , Kissimmee
This family-friendly townhome in Kissimmee is located within the Terra Verde resort, approximately 7 miles from Walt Disney World and 14.4 miles from Universal Studios.
This 3-bedroom, 2-bathroom rental accommodates up to 6 guests and features a private hot tub, a well-stocked kitchen, and access to resort amenities including a clubhouse, fitness center, and zero-entry pool.
Luxury 4br Villa With Private Pool For 10 Guests - Kissimmee, FL
9.9 134 reviews
Kissimmee, FL
07/26 – 07/30
$260/nighttotal: $1040 (4 )

Luxury 4br Villa With Private Pool For 10 Guests

4 8
house , Kissimmee
This Kissimmee vacation home is located in the Storey Lake Resort, approximately 16 minutes from Walt Disney World and 24 minutes from Universal Studios Florida.
The four-bedroom, three-bathroom house sleeps ten guests and boasts a private pool, access to resort amenities including a fitness center and lazy river, and a fully equipped kitchen.
Spacious 4br Pool Home Near Disney - Storey Lake - Kissimmee, FL
9.6 90 reviews
Kissimmee, FL
07/20 – 07/29
$192/nighttotal: $1728 (9 )

Spacious 4br Pool Home Near Disney - Storey Lake

4 7
apartment , Kissimmee
This Kissimmee vacation home boasts a prime location within three miles of Shingle Creek Regional Park, Kissimmee Go-Karts, and the 192 Flea Market, also near Medieval Times and Capone's Dinner Show.
This 1800-square-foot property features four bedrooms, three bathrooms, sleeps ten guests, and includes a private pool, fitness center, and free Wi-Fi; nearby attractions offer family fun.
161 Castaway Villa 4 Bed Pool&spa Resort - Kissimmee, FL
9.0 5 reviews
Kissimmee, FL
09/18 – 09/20
$267/nighttotal: $534 (2 )

161 Castaway Villa 4 Bed Pool&spa Resort

4 8
house , Kissimmee
This Kissimmee vacation home, located 8.2 miles from Gatorland, 10 miles from Disney Springs and Disney's Wide World of Sports, and 14 miles from Orlando International Airport, offers convenient access to major attractions.
This 10,760-square-foot property boasts four bedrooms, three bathrooms, and accommodates up to 15 guests, featuring a private pool, spa, fully equipped kitchen, and free Wi-Fi.

Best Kissimmee, FL vacation rentals with parking

The Perfect Getaway In Orlando - Kissimmee, FL
8.2 12 reviews
Kissimmee, FL
09/30 – 09/30
$271/nighttotal: $98915 (365 )

The Perfect Getaway In Orlando

1 11
apartment , Kissimmee
This spacious 3000 sq/ft villa in the 24/7 guarded gated community of Terra Verde Resort in Kissimmee is less than 10 miles from Magic Kingdom and other major Orlando attractions.
This professionally decorated residence offers 7 bedrooms accommodating up to 12 guests, a private screened-in lanai with a lake-view swimming pool, and access to extensive community amenities including a clubhouse, fitness center, and game room.
Charming 2-bedroom Florida Getaway! Sleeps 6 - Kissimmee, FL
9.8 15 reviews
Kissimmee, FL
07/03 – 07/05
$198/nighttotal: $396 (2 )

Charming 2-bedroom Florida Getaway! Sleeps 6

2 5
apartment , Kissimmee
This 2-bedroom, 2-bathroom private single-family home in Kissimmee is located within an RV resort community, offering convenient access to major attractions such as Aquatica, Universal Epic Universe, Epcot®, and Universal’s Volcano Bay, all within a 10-mile radius.
This accommodation sleeps up to 6 guests and features a full-sized washer and dryer, a private driveway, and access to resort amenities including a swimming pool, gym, and pickleball courts, providing a comfortable stay for theme park visitors.
Deluxe 4 Bedroom Home, South Facing Pool, 4460 , Pets Considered - Kissimmee, FL
9.1 113 reviews
Kissimmee, FL
12/10 – 12/23
$243/nighttotal: $3159 (13 )

Deluxe 4 Bedroom Home, South Facing Pool, 4460 , Pets Considered

4 2
apartment , Kissimmee
This 4-bedroom vacation rental is conveniently located in Bass Lakes Estates, just a short drive from popular attractions like Shingle Creek Regional Park, Give Kids the World Village, and the 192 Flea Market. This home has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This Kissimmee rental comfortably accommodates up to 8 guests and features a fully equipped kitchen, laundry facilities, and a private pool. Enjoy convenient amenities such as air conditioning, internet access, and parking, along with access to nearby entertainment options like Medieval Times and Kissimmee Go-Karts.
3br/3ba Townhome With Resort Pool, Clubhouse & Lake  Minutes From Disney - Kissimmee, FL
Kissimmee, FL
07/03 – 07/05
$312/nighttotal: $624 (2 )

3br/3ba Townhome With Resort Pool, Clubhouse & Lake Minutes From Disney

3 7
apartment , Kissimmee
This 3-bedroom, 3-bathroom apartment in Kissimmee is located within a 5-minute drive of Medieval Times and the 192 Flea Market, offering convenient access to Walt Disney World Resort, Disney's Hollywood Studios, and Epcot.
This 1280 sq ft vacation home accommodates up to 8 guests and features a fully equipped kitchen, in-unit laundry, Wi-Fi, air conditioning, a swimming pool, and a hot tub.

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.

Standard Four Beds Villas Seven Dwrafs - Close To Disney - Kissimmee, FL
8.6 12 reviews
Kissimmee, FL
12/23 – 12/31
$270/nighttotal: $2160 (8 )

Standard Four Beds Villas Seven Dwrafs - Close To Disney

4 7
house , Kissimmee
This Kissimmee vacation home is conveniently located seven miles from Gatorland and Disney Springs, with easy access to Disney's Wide World of Sports Complex and Disney's Boardwalk.
This 1,450-square-foot villa boasts four bedrooms, three bathrooms, sleeps fifteen guests, and includes a private pool, spa, tennis court, and fitness center.
Gorgeous 4bd W/ Pool Close To Disney @ Storey Lake 4289 - Kissimmee, FL
9.2 66 reviews
Kissimmee, FL
08/28 – 09/05
$240/nighttotal: $1920 (8 )

Gorgeous 4bd W/ Pool Close To Disney @ Storey Lake 4289

4 12
house , Kissimmee
This Kissimmee vacation home is located eight miles from Gatorland and Disney Springs, offering convenient access to major attractions.
This 1980-square-foot property boasts four bedrooms, three bathrooms, a private pool, and on-site amenities including a fitness center and tennis court, comfortably accommodating families or groups.
Vacation Home In Orlando Florida United States - Kissimmee, FL
8.9 26 reviews
Kissimmee, FL
09/08 – 09/12
$232/nighttotal: $928 (4 )

Vacation Home In Orlando Florida United States

4 2
house , Kissimmee
This Kissimmee vacation home is conveniently located just a short drive from popular attractions like Gatorland and Disney's Wide World of Sports, making it an ideal choice for families visiting the area. The home has received excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom, three-bathroom property offers ample space for families or groups. Enjoy a refreshing dip in the private pool, relax in the Jacuzzi, or cook meals in the fully equipped kitchen.
New Luxury 15 Bedrooms15baths At Veranda Palms - Kissimmee, FL
Kissimmee, FL
06/29 – 07/05
$1388/nighttotal: $8328 (6 )

New Luxury 15 Bedrooms15baths At Veranda Palms

15 25
house , Kissimmee
This vacation home in Kissimmee is located in the Veranda Palms community, 7.8 miles from Disney Springs and 8.3 miles from Disney's Wide World of Sports.
This expansive property offers 15 bedrooms, 15 bathrooms, and a guest capacity of 59, featuring air conditioning, a private pool, a terrace, and complimentary WiFi.

Best Kissimmee, FL vacation rentals with air conditioning

Newly Renovated - Family Friendly - Backs Onto Pond - Wifi - Close To Disney - Kissimmee, FL
9.0 53 reviews
Kissimmee, FL
08/10 – 08/24
$147/nighttotal: $2058 (14 )

Newly Renovated - Family Friendly - Backs Onto Pond - Wifi - Close To Disney

3 2
apartment , Kissimmee
This newly renovated three-bedroom townhouse is located in the gated Terra Verde resort community in Kissimmee, Florida, approximately 10 minutes from Walt Disney World and 25 minutes from Orlando International Airport.
The 1300-square-foot property boasts a private hot tub, access to resort amenities including a heated pool and Tiki bar, and sleeps six guests comfortably, featuring three smart TVs and a fully equipped kitchen.
Euphoria 1br King Suite | Resort Pool • Disney C - Kissimmee, FL
9.8 40 reviews
Kissimmee, FL
12/25 – 01/07
$112/nighttotal: $1456 (13 )

Euphoria 1br King Suite | Resort Pool • Disney C

1 2
apartment , Kissimmee
This one-bedroom Kissimmee condo is ideally located in a gated resort community near Disney World, offering easy access to theme parks and beaches.
The 1-bedroom, 1-bathroom unit sleeps 4 guests and boasts a fully equipped kitchen with a Keurig, two smart TVs (45-inch and 60-inch), a king-size memory foam bed, resort amenities including pools, a hot tub, and fitness center, plus proximity to Shingle Creek Regional Park Trail.
Luxe Condo Double Bed Bliss Getaway Near Disney - Kissimmee, FL
8.6 40 reviews
Kissimmee, FL
08/14 – 08/16
$146/nighttotal: $292 (2 )

Luxe Condo Double Bed Bliss Getaway Near Disney

1 2
apartment , Kissimmee
This Kissimmee condo rental is located in a gated resort community, 15-20 minutes from Walt Disney World and provides easy access to Old Town, Orlando Vineland Premium Outlets, Aquatica, and Epcot.
The first-floor unit sleeps five guests comfortably in two full-size beds and features a fully equipped kitchen with a Keurig coffee maker, two 65-inch smart TVs, a full bath with shower/tub combo, and resort amenities including a swimming pool and jacuzzi.
Family Friendly Villa, Gated Community, Spa, Heated Pool, Close To Theme Parks. - Kissimmee, FL
9.6 199 reviews
Kissimmee, FL
08/17 – 08/24
$177/nighttotal: $1239 (7 )

Family Friendly Villa, Gated Community, Spa, Heated Pool, Close To Theme Parks.

3 3
apartment , Kissimmee
This family-friendly vacation home in Kissimmee is conveniently located near popular attractions like Medieval Times, Give Kids the World Village, and Kissimmee Go-Karts, all within a 3-mile radius. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This 3-bedroom vacation rental spans 1280 square feet and comfortably accommodates up to 8 guests. Enjoy a range of amenities including a private pool, jacuzzi, sauna, spa, fitness center, tennis court, and a fully equipped kitchen, perfect for creating memorable moments with loved ones.
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