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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.

24/7 Gated 6 /3.5 Bath Off 192,pool, Tennis 1073 - Kissimmee, FL
10 57 reviews
Kissimmee, FL
09/13 – 09/23
$198/nighttotal: $1980 (10 )

24/7 Gated 6 /3.5 Bath Off 192,pool, Tennis 1073

1 2
apartment , Kissimmee
This Kissimmee vacation home is located a few blocks from US-192, offering easy access to theme parks, restaurants, and shopping while maintaining a quiet, secluded atmosphere.
This six-bedroom, three-and-a-half-bathroom villa sleeps twelve guests and features a private pool, game room, dedicated children's theme rooms, and a gated community with 24/7 security.
Roomy House Near Disney + Resort Pool + Patio Bbq - Kissimmee, FL
9.2 5 reviews
Kissimmee, FL
07/15 – 07/19
$203/nighttotal: $812 (4 )

Roomy House Near Disney + Resort Pool + Patio Bbq

3 1
apartment , Kissimmee
This Kissimmee vacation home, located in a rural area near a lake and a short drive from major theme parks like Disney World and Universal Studios, offers convenient access to supermarkets, restaurants, Reunion Resort and Mystic Dunes golf courses, Old Town, and ESPN Wide World of Sports.
This 1,500-square-foot property features a spacious family-friendly layout, accommodating up to 7 guests, with 3 bedrooms, 3 bathrooms, a private pool, a tennis court, and a sauna, along with all the amenities needed for a comfortable stay.
Private Resort Access~king Bed~hot Tub~balcony - Kissimmee, FL
10 1 review
Kissimmee, FL
07/05 – 08/04
$161/nighttotal: $4830 (30 )

Private Resort Access~king Bed~hot Tub~balcony

3 1
apartment , Kissimmee
This townhome offers Private Resort Access with a king bed, hot tub, and balcony, located in the gated Lake Berkley Resort Villas Phase 2 community in Kissimmee, a short drive from Walt Disney World Resort and other major theme parks.
This family-friendly resort villa accommodates up to 8 guests across 3 bedrooms and 2 bathrooms, featuring a private balcony, a fully equipped kitchen, and exclusive access to a community pool, all within 1 mile of shopping centers and dining options.
4br Townhome With Lake View – Bl481 - Kissimmee, FL
9.2 57 reviews
Kissimmee, FL
12/01 – 12/08
$217/nighttotal: $1519 (7 )

4br Townhome With Lake View – Bl481

4 2
house , Kissimmee
This Kissimmee vacation home, located approximately 7-10 miles from Disney parks and Gatorland, offers easy access to major attractions like Disney's Hollywood Studios, Blizzard Beach, Disney Springs, and Disney's Boardwalk.
The 1910-square-foot property features four bedrooms, a private pool, a fully equipped kitchen with a dishwasher, free Wi-Fi, and parking, perfect for families or groups seeking a comfortable and convenient stay near Orlando's theme parks.

Best Kissimmee, FL vacation rentals with parking

Charming 3bd/2.5ba * Jacuzzi + Lake View - Kissimmee, FL
10 2 reviews
Kissimmee, FL
11/05 – 11/08
$243/nighttotal: $729 (3 )

Charming 3bd/2.5ba * Jacuzzi + Lake View

3 6
house , Kissimmee
This Kissimmee vacation rental is conveniently located 8-11 miles from Disney World parks, including Disney's Hollywood Studios and Disney Springs, and 8.5 miles from Gatorland.
The 3-bedroom, 3-bathroom condo sleeps 8, features a fully equipped kitchen with dishwasher, in-unit jacuzzi, and access to a community pool, fitness center, and free Wi-Fi; enjoy a lake view from your private balcony.
14 Mi To Disney World: Kissimmee Condo W/ Perks! - Kissimmee, FL
10 5 reviews
Kissimmee, FL
07/05 – 08/04
$162/nighttotal: $4860 (30 )

14 Mi To Disney World: Kissimmee Condo W/ Perks!

4 1
apartment , Kissimmee
This Kissimmee vacation rental, located in the Venetian Bay Villages community, is 4 miles from Kissimmee Lakefront Park, 14 miles from Walt Disney World, and 16 miles from Universal Studios.
This 1470-square-foot, five-bedroom, three-bathroom condo sleeps eight guests and features a well-equipped kitchen, in-unit laundry, a swimming pool, a jacuzzi, free community parking, and proximity to community amenities including tennis, basketball, and volleyball courts.
Comfortable Vacation Pool Home, 10 Mins To Walt Disney World® Resort! - Kissimmee, FL
9.2 5 reviews
Kissimmee, FL
07/15 – 08/27
$150/nighttotal: $6450 (43 )

Comfortable Vacation Pool Home, 10 Mins To Walt Disney World® Resort!

3 4
apartment , Kissimmee
This Kissimmee vacation home is located in the peaceful Indian Point neighborhood, less than a mile from Give Kids the World Village and Shingle Creek Regional Park, and within two miles of the 192 Flea Market and Medieval Times.
This 1,330-square-foot house features three bedrooms, two bathrooms, a private pool, and sleeps six guests comfortably, with added amenities including a fully equipped kitchen, free Wi-Fi, and an on-site game room.
178 M² House ∙ 4 Bedrooms ∙ 10 Guests - Kissimmee, FL
Kissimmee, FL
07/31 – 09/01
$179/nighttotal: $5728 (32 )

178 M² House ∙ 4 Bedrooms ∙ 10 Guests

4 2
house , Kissimmee
This 4-bedroom, 3-bathroom house in Kissimmee's Storey Lake Resort is located 10-15 minutes from Walt Disney World, 15 minutes from SeaWorld, and 20-25 minutes from Universal Studios.
This 1910 square foot vacation home accommodates up to 10 guests with a fully equipped kitchen, air conditioning, Wi-Fi, a private outdoor space, and includes a high chair and Pack 'n Play, with access to a community swimming pool and fitness center.

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.

Coastal Theme 4-bedroom House With Ac In Sunny Kissimmee - Kissimmee, FL
Kissimmee, FL
07/02 – 07/05
$419/nighttotal: $1257 (3 )

Coastal Theme 4-bedroom House With Ac In Sunny Kissimmee

4 10
apartment , Kissimmee
This coastal-themed vacation home is located in Kissimmee's Bellavida neighborhood, offering convenient access to Walt Disney World Resort (under 20 minutes) and Universal Studios (under 25 minutes).
This spacious 3200 sq ft rental accommodates up to 12 guests with four bedrooms and two sofa beds, featuring a private heated pool, BBQ grill, and daily valet garbage service.
Disney Kissimmee Condo - Kissimmee, FL
8.6 25 reviews
Kissimmee, FL
07/23 – 07/26
$150/nighttotal: $450 (3 )

Disney Kissimmee Condo

3 2
apartment , Kissimmee
This Kissimmee condo, located approximately 7 miles from Disney Springs and Gatorland, offers easy access to major theme parks.
This 1190-square-foot vacation rental boasts three bedrooms, two bathrooms, and accommodates up to 13 guests, featuring a fully equipped kitchen, free Wi-Fi, and a private terrace.
Beautiful Lake View Golf Home 2723 - Kissimmee, FL
9.5 103 reviews
Kissimmee, FL
07/02 – 07/05
$333/nighttotal: $999 (3 )

Beautiful Lake View Golf Home 2723

4 8
apartment , Kissimmee
This Kissimmee vacation rental is located just 2 miles from Remington Golf Club, Osceola Center for the Arts, and Osceola Flea and Farmers Market, making it a great base for exploring the area. The house has received excellent ratings for location, cleanliness, and overall user experience.
The 4-bedroom home comfortably accommodates 8 guests and features a spacious dining area. Enjoy a refreshing dip in the private pool, relax on the terrace, and take advantage of amenities like a fully equipped kitchen, a washing machine, and internet access.
4200 Paragraph Drive - Kissimmee, FL
9.3 73 reviews
Kissimmee, FL
07/26 – 07/30
$286/nighttotal: $1144 (4 )

4200 Paragraph Drive

5 8
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.

Best Kissimmee, FL vacation rentals with air conditioning

Sunshine Serenity By Paradise Resort Vacations - Kissimmee, FL
10 1 review
Kissimmee, FL
07/03 – 07/05
$508/nighttotal: $1016 (2 )

Sunshine Serenity By Paradise Resort Vacations

4 10
house , Kissimmee
This Kissimmee villa is located approximately 9 miles from Disney's Hollywood Studios, Disney's Boardwalk, and Disney Springs, and 8.4 miles from Gatorland.
This 1940 square foot house offers 4 bedrooms, 3 bathrooms, and accommodates up to 19 guests with a private swimming pool, hot tub, free Wi-Fi, and free private parking.
Fantastic Mickey House Waterpark Near Disney 2572 - Kissimmee, FL
9.7 71 reviews
Kissimmee, FL
07/10 – 07/18
$249/nighttotal: $1992 (8 )

Fantastic Mickey House Waterpark Near Disney 2572

4 7
apartment , Kissimmee
This luxurious four-bedroom, three-bathroom townhouse is located in the Story Lake Resort Community in Kissimmee, Florida, minutes from Disney World theme parks and offering free access to a nearby water park.
The 8-guest property boasts a private screened-in pool (heating optional, fee applies), a fully equipped kitchen, in-house laundry, smart TVs with Spectrum app access, and self check-in.
3bd 2ba Luxe Villa Located 20 Minutes From Disney - Kissimmee, FL
9.6 110 reviews
Kissimmee, FL
07/03 – 07/05
$287/nighttotal: $574 (2 )

3bd 2ba Luxe Villa Located 20 Minutes From Disney

1 5
house , Kissimmee
This Kissimmee villa offers a convenient location near major attractions, with theme parks like Walt Disney World, Universal Studios, and SeaWorld within a 20-25 minute drive and shopping centers such as Publix, Walmart, The LOOP Mall, and The Crosslands Mall a short 5-15 minute drive away.
This three-bedroom, two-bathroom house sleeps six guests and features an open-concept living, dining, and kitchen area with modern appliances, a heated community pool within a two-minute walk, reserved parking, and a second bedroom with a 43” Smart HDTV, Xbox, and workspace.
Fun Packed 5 Bedroom Villa With Private Pool/spa, Games Room & Grill - Kissimmee, FL
9.1 60 reviews
Kissimmee, FL
10/31 – 11/07
$248/nighttotal: $1736 (7 )

Fun Packed 5 Bedroom Villa With Private Pool/spa, Games Room & Grill

5 4
house , Kissimmee
This Lake Berkley villa in Kissimmee offers convenient access to Medieval Times and the 192 Flea Market (under 1 mile), Give Kids the World Village, and Capone's Dinner Show (under 3 miles).
This spacious 5-bedroom, 2340-square-foot vacation home boasts a private pool, on-site water park, fitness center, spa, and numerous family-friendly amenities including a game room, garden, and barbecue grills.
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