Holiday Rentals in Kissimmee, FL

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Kissimmee, FL holiday rentals
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15321 Holiday rentals and Airbnb in Kissimmee, FL

Best family friendly Kissimmee, FL holiday rentals

Among the 15321 accommodations in Kissimmee, FL, here are the 4 best family friendly rentals

Your Orlando Getaway Lakefront Villa With Pool, Only 15min To Disney @Terraverde - Kissimmee, FL
9.3 136 reviews
Kissimmee, FL
18/10 – 25/10
143 €/nighttotal: 1001 € (7 )

Your Orlando Getaway Lakefront Villa With Pool, Only 15min To Disney @Terraverde

4 2
apartment , Kissimmee
This four-bedroom, three-bathroom townhome in the Terra Verde Resort, Kissimmee, is approximately 32km from Walt Disney World Resort and 40km from Universal Orlando Resort.
The property boasts a private swimming pool, fitness centre, and fully equipped kitchen, sleeping up to eight guests and offering access to resort amenities including a clubhouse and parking; recent upgrades include a smart TV and improved kitchenware.
4 Bedroom 3 Bathroom Villas At Seven Dwarfs 17-101 - Kissimmee, FL
9.7 7 reviews
Kissimmee, FL
22/07 – 02/08
120 €/nighttotal: 1320 € (11 )

4 Bedroom 3 Bathroom Villas At Seven Dwarfs 17-101

1 7
apartment , Kissimmee
This Kissimmee villa, located in the Villas at Seven Dwarfs resort, is approximately 16km from Walt Disney World Resort, 26km from SeaWorld Orlando, and 34km from Universal Orlando Resort.
The 1470 sq ft property offers four bedrooms, three bathrooms, sleeps eight guests, and includes a private pool, fitness centre access, and a fully equipped kitchen; free baby equipment is provided.
Beautiful  Apartment 3br-2bath - Close To Disney - Kissimmee, FL
Kissimmee, FL
15/07 – 27/08
91 €/nighttotal: 3913 € (43 )

Beautiful Apartment 3br-2bath - Close To Disney

3 4
apartment , Kissimmee
This 3-bedroom holiday flat in the Club Cortile community, Kissimmee, is just 6 kilometres from Walt Disney World Resort and a short drive to Old Town and popular theme parks, with golf courses like Mystic Dunes and Reunion Resort nearby.
This accommodation offers 111 square meters of space for up to 8 guests, featuring a fully equipped kitchen, free WiFi, air conditioning, a swimming pool, and access to community amenities including a spa, gym, and playground.
House Orlando - Kissimmee, FL
9.5 89 reviews
Kissimmee, FL
24/07 – 26/07
222 €/nighttotal: 444 € (2 )

House Orlando

1 6
house , Kissimmee
This Bela Vida condominium property in Kissimmee, Florida, is situated a 5km drive from Walmart and Chick-fil-A, and a 24km drive from the Disney parks, offering convenient access to shopping outlets and attractions.
Sleeping nine guests, this four-bedroom, three-bathroom house boasts a private pool, barbecue area, and access to a community pool, jacuzzi, cinema room, and games room within the Bela Vida complex; it also includes a fully equipped kitchen and in-house laundry facilities.

Best Kissimmee, FL holiday rentals with parking

Storey Lake Resort~heated Pool~brand New~designer - Kissimmee, FL
10 2 reviews
Kissimmee, FL
04/08 – 18/08
165 €/nighttotal: 2310 € (14 )

Storey Lake Resort~heated Pool~brand New~designer

4 4
house , Kissimmee
This family-friendly townhome is located in Storey Lake, Kissimmee, offering convenient access, just 6 minutes by car from Walt Disney World Resort and a short drive to Universal Studios and SeaWorld.
This 176 square metre residence features 4 bedrooms and 3 bathrooms, accommodating up to 10 guests with a private screened swimming pool, complimentary WiFi, and access to the Storey Lake resort's amenities including a lazy river and gym.
Calypso Cay Vacation Villas - Kissimmee, FL
8.4 7953 reviews
Kissimmee, FL
03/07 – 05/07
591 €/nighttotal: 1182 € (2 )

Calypso Cay Vacation Villas

3 17
resort , Hunters Creek
Calypso Cay Vacation Villas are located in Hunters Creek, just a short drive from Disney World, SeaWorld and Universal Studios. The resort has received very good ratings for its location, cleanliness and overall experience.
The villas offer comfortable and self-sufficient accommodation with fully equipped kitchens. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, fitness centre, restaurant and bar.
Comfortable Stay Near Disney Parks 2 - Kissimmee, FL
Kissimmee, FL
01/07 – 03/07
188 €/nighttotal: 376 € (2 )

Comfortable Stay Near Disney Parks 2

1 2
apartment , Kissimmee
This Kissimmee townhouse is located within the secure, gated Lake Berkley Resort, offering convenient access to premier shopping and dining at The Loop, located just 1.6 kilometres away, and is a short drive from Walt Disney World Resort and other Orlando attractions.
This accommodation provides comfortable lodging for up to six guests, featuring two king beds and two twin beds, a fully equipped kitchen, in-unit laundry facilities, and complimentary high-speed Wi-Fi, with full resort access including community swimming pools, a fitness centre, tennis and basketball courts, and walking trails.
Stunning 3bd Condo 14 Mins To Disney World L Gated - Kissimmee, FL
9.5 140 reviews
Kissimmee, FL
13/12 – 03/01
171 €/nighttotal: 3591 € (21 )

Stunning 3bd Condo 14 Mins To Disney World L Gated

3 6
apartment , Kissimmee
This three-bedroom, two-bathroom Kissimmee condo, situated near major highways (192 and I-4), offers easy access to Orlando's theme parks (Disney World, Universal Orlando Resort, SeaWorld), the Orlando Convention Center, and is approximately 72km from Cocoa Beach and NASA.
The ground-floor apartment sleeps six, boasts a fully equipped kitchen including a dishwasher, features a swimming pool, jacuzzi and fitness centre, and provides complimentary cot for infants; nearby amenities include Sam's Club and Target.

Frequently asked questions about holiday rentals in Kissimmee, FL

  • Which neighborhood in Kissimmee should you consider for a vacation rental?

    If you're looking for a vacation rental, the area around Celebration is a good bet. It's close to the theme parks and has a lovely, family-friendly atmosphere with plenty of restaurants and shops. You might also consider the Reunion area, which offers a good range of luxury rentals.
  • What are the best Airbnb and holiday rentals in Kissimmee, FL?

  • 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.

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

    Kissimmee is a haven for families! You've got the big hitters like Disney World, Universal Studios, and SeaWorld, but don't forget about the smaller attractions like Gatorland, the Dinosaur World, and the Fun Spot America amusement park. These offer a different experience from the big theme parks and are great for all ages.
  • What are the most popular Airbnbs in Kissimmee, FL?

  • 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.

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

    To get the best deals, book your vacation rental well in advance, especially if you're travelling during peak season, which is typically from mid-December to mid-April. You can also try booking during the shoulder season (April-May and September-October) for better rates and fewer crowds.
  • What are the best holiday rentals with a pool in Kissimmee, FL?

  • 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 events or festivals should visitors check out in and around Kissimmee?

    Kissimmee has a vibrant events calendar throughout the year. The Osceola County Fair in February is a local favourite, and the Epcot International Food & Wine Festival in the autumn is a massive event that attracts visitors from all over. You can find a full list of events on the Kissimmee Convention and Visitors Bureau website.
  • What are the best rentals for families and kids in Kissimmee, FL?

  • 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 budget-friendly activities in Kissimmee?

    There are plenty of free and budget-friendly activities in Kissimmee. Head to the Lakefront Park for a picnic and a stroll, or visit the Kissimmee Air Museum for a glimpse into aviation history. The Osceola Heritage Park also offers free events throughout the year.
  • What are the best rentals or Airbnbs with a jacuzzi in Kissimmee, FL?

  • 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.

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

    For authentic Floridian cuisine, try the Dixie Crossroads in Titusville, just a short drive from Kissimmee. They're famous for their seafood, especially their stone crab claws. If you're looking for something closer to Kissimmee, try the Bob Evans restaurant on West Irlo Bronson Memorial Highway for a taste of classic American comfort food.
  • What are the best walking or cycling routes in Kissimmee?

    The East Lake Tohopekaliga Loop is a great option for a leisurely bike ride, offering scenic views of the lake and the surrounding nature. For a shorter walk, the Celebration Town Center is a lovely area to stroll around, with its charming shops and restaurants.
  • Are there pet-friendly attractions in Kissimmee?

    Yes, many attractions in Kissimmee are pet-friendly. The Promenade at Celebration is a great place to walk your dog, and the Osceola Heritage Park often hosts dog-friendly events. Check with individual attractions for their pet policies before you go.

Destinations nearby

Best Kissimmee, FL holiday rentals with a balcony

120 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Kissimmee, FL
10 1 review
Kissimmee, FL
27/06 – 04/07
198 €/nighttotal: 1386 € (7 )

120 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests

2 3
apartment , Hunters Creek
This Hunters Creek flat is located in the Storey Lake Resort area of Orlando, approximately 8 kilometres from Walt Disney World Resort, 11 kilometres from Universal Studios Florida and 11 kilometres from SeaWorld Orlando.
This 120 square metre condo offers accommodation for up to five guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, complimentary WiFi, a private balcony with resort views, and access to resort amenities including a swimming pool and fitness centre.
3br 3bath Townhome Bbq Pool 15min Disney 1291ft - Kissimmee, FL
8.8 51 reviews
Kissimmee, FL
10/10 – 17/10
194 €/nighttotal: 1358 € (7 )

3br 3bath Townhome Bbq Pool 15min Disney 1291ft

3 3
house , Kissimmee
This Kissimmee townhouse, located 15 minutes' drive (approx. 24 km) from Walt Disney World, 11.7 km from Gatorland, and 13.8 km from Disney's Wide World of Sports, offers convenient access to major attractions.
The 120-square-metre property boasts three bedrooms and three bathrooms, sleeping up to six guests, and includes a private swimming pool, Jacuzzi, and terrace alongside free Wi-Fi, parking, and on-site fitness centre.
New Listing! Storey Lake Resort, 6mi To Disney & 11mi To Universal - Grh596616 - Kissimmee, FL
Kissimmee, FL
10/07 – 24/07
789 €/nighttotal: 11046 € (14 )

New Listing! Storey Lake Resort, 6mi To Disney & 11mi To Universal - Grh596616

8 15
resort , Kissimmee
New Listing! Storey Lake Resort, GRH596616, is a centrally located Kissimmee holiday home, approximately 3km from Shingle Creek Regional Park and Capone's Dinner & Show, and under 5km from Kissimmee Go-Karts and Give Kids the World Village.
This eight-bedroom, six-bathroom villa boasts 372 square metres of space, accommodating up to 16 guests and offering a private pool, water park access, fitness centre, hot tub, and concierge services.
New Listing! Crystal Cove Resort, 6mi To Disney & 11mi To Universal - 71 - Kissimmee, FL
8.9 67 reviews
Kissimmee, FL
13/07 – 17/07
355 €/nighttotal: 1420 € (4 )

New Listing! Crystal Cove Resort, 6mi To Disney & 11mi To Universal - 71

7 15
resort , Kissimmee
This spacious house is located in the Crystal Cove Resort community in Kissimmee, Florida, just a short drive from popular attractions like Gatorland and Disney's Wide World of Sports. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers five bedrooms, a living room, a fully equipped kitchen, and four bathrooms, providing ample space for families or groups. Guests can enjoy a range of amenities, including a swimming pool, a Jacuzzi, a fitness centre, a tennis court, and a patio for outdoor relaxation.

Best Kissimmee, FL holiday rentals with air conditioning

Orlando Area - Relaxing 4 Bedroom Home With Pool & Water View - Kissimmee, FL
9.7 142 reviews
Kissimmee, FL
27/07 – 04/08
140 €/nighttotal: 1120 € (8 )

Orlando Area - Relaxing 4 Bedroom Home With Pool & Water View

1 4
apartment , Kissimmee
This four-bedroom Kissimmee holiday home boasts a waterfront location, within 5km of Green Meadows Petting Farm, Give Kids the World Village, and Shingle Creek Regional Park, and 10km from Old Town and Kissimmee Go-Karts.
Sleeping up to nine guests, the property offers a private pool, a fully equipped kitchen, free Wi-Fi, and a fenced yard with barbecue facilities, ideal for families seeking convenient access to major attractions.
Disney 8mi~heated Resort Pool~hot Tub~fitness - Kissimmee, FL
10 12 reviews
Kissimmee, FL
15/07 – 27/08
92 €/nighttotal: 3956 € (43 )

Disney 8mi~heated Resort Pool~hot Tub~fitness

1 4
apartment , Kissimmee
This three-bedroom townhouse is situated within the secure, gated Villas at Seven Dwarfs Resort in Kissimmee, Florida, offering convenient access to Walt Disney World Resort and Universal Studios Florida, both located just a few kilometres away.
This family-friendly accommodation sleeps up to six guests and features a fully equipped kitchen, air conditioning, in-unit laundry, a jacuzzi, and access to resort amenities including a heated pool and fitness centre.
Beautiful Lake View Golf Home 2723 - Kissimmee, FL
9.5 103 reviews
Kissimmee, FL
04/07 – 18/07
224 €/nighttotal: 3136 € (14 )

Beautiful Lake View Golf Home 2723

4 4
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.
Lovely House Near Theme Parks - Kissimmee - Kissimmee, FL
9.3 234 reviews
Kissimmee, FL
05/11 – 08/11
215 €/nighttotal: 645 € (3 )

Lovely House Near Theme Parks - Kissimmee

4 6
apartment , Kissimmee
This luxury villa, situated in the Crystal Cove Resort in Kissimmee, Florida, is approximately 24 kilometres from Walt Disney World and other Orlando attractions.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a south-facing pool, a game room with pool table, foosball, hockey and ping pong tables, a fully equipped kitchen, free Wi-Fi, and private parking for three cars.
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