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

Spacious 1 Bedroom Loft In Disney Area 5 Star Rated Mill Creek Resort 2767 - Kissimmee
9.4 32 reviews

Spacious 1 Bedroom Loft In Disney Area 5 Star Rated Mill Creek Resort 2767

resort, Kissimmee
This Kissimmee holiday property, '1 Bedroom With Loft Disney Area Vacation Rental Award Winning Mill Creek Resort', is conveniently located within 5km of the Osceola Performing Arts Centre, Tupperware Brands World Headquarters, and Osceola Regional Medical Center, and within 10km of Lake Tohopekaliga and Silver Spurs Arena.
The two-bedroom, one-bathroom self-catering villa sleeps six guests and boasts a swimming pool, hot tub, fitness centre, and terrace; pets are welcome.
The Hearth Home - 4 Suites - Kissimmee
10 2 reviews

The Hearth Home - 4 Suites

house, Kissimmee
This spacious 191 sqm villa in Kissimmee is situated 6.7 kilometres from Gatorland and 17.7 kilometres from Florida Mall, placing it 17.7 kilometres from Orlando International Airport.
This family-friendly property offers accommodation for 22 guests with four bedrooms, each featuring a private bathroom, and includes a private outdoor swimming pool, jacuzzi, spa facilities, a fitness centre, a garden, a terrace, and a children's playground.
15 Min To Disney | 3br| Resort Pool - Kissimmee
9.4 71 reviews

15 Min To Disney | 3br| Resort Pool

house, Kissimmee
This Kissimmee holiday home is located minutes (approximately 1-2 km) from Walt Disney World and offers free access to the Seven Dwarfs Mine Train resort amenities.
Sleeping six guests, this three-bedroom, two-bathroom property boasts themed bedrooms (Toy Story and Star Wars), a private pool, jacuzzi, fitness centre, and fully equipped kitchen; free WiFi and parking are also included.
Brightwatervilla. Lake View, West Facing Extra Large Pool Deck, Lanai, Hot Tub - Kissimmee
9.6 88 reviews

Brightwatervilla. Lake View, West Facing Extra Large Pool Deck, Lanai, Hot Tub

house, Kissimmee
This five-bedroom villa is located in Kissimmee, just a short distance from the waterfront and within easy reach of attractions like Give Kids the World Village and Shingle Creek Regional Park. It has received excellent user ratings, making it a popular choice for families and groups.
The spacious villa, measuring 270 square metres, comfortably accommodates up to 11 guests. With a private pool, jacuzzi, tennis court, and a fully equipped kitchen, it offers a range of amenities and activities for a relaxing and enjoyable stay.

Best Kissimmee vacation rentals with parking

Yacht & Beach Themed Gorgeous Villa! - Kissimmee
9.3 55 reviews

Yacht & Beach Themed Gorgeous Villa!

apartment, Kissimmee
This luxury yacht near Walt Disney World in Kissimmee, Florida offers easy access to numerous restaurants and shops, providing a prime location for exploring the area.
Sleeping six guests across three bedrooms and two bathrooms, this self-catering vessel boasts a private solar-heated swimming pool, a fully equipped kitchen including dishwasher, and complimentary Wi-Fi, ensuring a comfortable and convenient stay.
Bellavida-amazing 5br4ba Home*pool/spa*gated - Kissimmee
8.8 51 reviews

Bellavida-amazing 5br4ba Home*pool/spa*gated

house, Kissimmee
Bella Vida (891mb), a five-bedroom, four-bathroom holiday home in Kissimmee, Florida, is situated within 1.6km of Medieval Times, the 192 Flea Market, and Shingle Creek Regional Park, and within 4.8km of Give Kids the World Village and Kissimmee Go-Karts.
This 191 square metre property sleeps up to 12 guests and boasts a private pool, spa, fully equipped kitchen, laundry facilities, and access to an on-site water park; additional amenities include a patio, Smart TV, and a fitness centre.
Carri-vision Suite, (Theme-parks)orlando/kissimmee - Kissimmee
9.8 67 reviews

Carri-vision Suite, (Theme-parks)orlando/kissimmee

apartment, Kissimmee
This Kissimmee apartment, ideally located within the city's loop, offers easy access to major attractions such as Walt Disney World (22km), Universal Studios Florida (15km), and SeaWorld Orlando (10km).
The one-bedroom flat sleeps three, boasts a fully equipped kitchen with dishwasher, in-unit laundry, a swimming pool, fitness centre and free Wi-Fi, providing a comfortable base for exploring the theme parks and nearby Gatorland (5km).
Sunset Bliss Retreat Condo - Near Disney - Kissimmee
9.6 57 reviews

Sunset Bliss Retreat Condo - Near Disney

apartment, Kissimmee
This Kissimmee apartment, located in a gated resort community 24-32km from Walt Disney World and near Reunion Resort Golf Course and Mystic Dunes Golf Club, offers easy access to Old Town and Orlando Vineland Premium Outlets.
The 71 square metre self-catering property features one bedroom, one bathroom, sleeps four, and includes a king-size bed, 65-inch smart TVs, a fully equipped kitchen, a swimming pool, a jacuzzi, and a terrace.

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

Cozy 3br Townhome - Pool - Bella Vida Resort - Kissimmee
No reviews

Cozy 3br Townhome - Pool - Bella Vida Resort

apartment, Kissimmee
This Bella Vida Resort townhome in Kissimmee, Florida, is situated approximately 27 kilometres from Walt Disney World and 48 kilometres from Universal Studios Florida.
The 'Charming 3br Resort Townhome With Pool & BBQ Area!' offers 120 square metres of living space, sleeping up to seven guests across three bedrooms and two bathrooms, and includes a private pool, BBQ grill, and access to resort amenities such as a clubhouse, fitness centre, and playground.
Jc Disney House - Kissimmee
9.1 16 reviews

Jc Disney House

resort, Kissimmee
JC Disney House, a Kissimmee holiday villa, is situated approximately 12.2 kilometres from Gatorland, 14 kilometres from Disney's Wide World of Sports, and 14.3 kilometres from Disney's Hollywood Studios.
This 111-square-metre property boasts three bedrooms, three bathrooms, a private patio with barbecue, and sleeps up to eleven guests, offering access to a shared pool, fitness centre, and tennis court.
Upstay - Pet-friendly Resort Townhouse W Patio - Kissimmee
No reviews

Upstay - Pet-friendly Resort Townhouse W Patio

apartment, Kissimmee
This apartment is centrally located in downtown Kissimmee, a 5-minute drive from Medieval Times and the 192 Flea Market.
This family-friendly rental offers 119 square meters of living space with 3 bedrooms and 3 bathrooms, accommodating up to 6 guests with amenities including a shared swimming pool, hot tub, and fitness centre.
The Villa At Terra Verde - Kissimmee
9.6 111 reviews

The Villa At Terra Verde

house, Kissimmee
The Villa at Terra Verde is situated in Kissimmee, just nine miles from both Gatorland and Disney's Wide World of Sports, making it a convenient base for exploring the area's attractions. This property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This spacious six-bedroom villa can comfortably accommodate up to 13 guests, offering plenty of room for families or groups of friends. The villa boasts a private pool and patio, a fully equipped kitchen, and a range of wellness amenities including a sauna, hot tub, and fitness room, ensuring a relaxing and enjoyable stay.

Best Kissimmee vacation rentals with air conditioning

Beautiful 4bd/3ba Townhome With Pool 280 - Kissimmee
9.3 79 reviews

Beautiful 4bd/3ba Townhome With Pool 280

house, Kissimmee
This four-bedroom house near Disney World in Kissimmee, Florida, is a short 5-6 minute (approx. 5 km) drive from the Storey Lake Hideaway Clubhouse, offering convenient access to its amenities.
Sleeping up to 12 guests, this self-catering property boasts a private pool, fitness centre, and full kitchen with dishwasher, plus a washer and dryer; optional grill rental and pet-friendly policy (with cleaning fee) apply.
Crystal Cove !  Gated Community Private Pool Home. - Kissimmee
9.8 58 reviews

Crystal Cove ! Gated Community Private Pool Home.

apartment, Kissimmee
This Crystal Cove holiday home in Kissimmee is conveniently located within 1.6km of Medieval Times and the 192 Flea Market, and within 4.8km of Shingle Creek Regional Park and Give Kids the World Village.
Sleeping eight guests, this four-bedroom, three-bathroom property boasts a private pool, fully equipped kitchen, on-site fitness centre and spa, plus easy access to a water park.
5br 3bath Private Townhome 13min Disney 1496ft - Kissimmee
9.2 33 reviews

5br 3bath Private Townhome 13min Disney 1496ft

house, Kissimmee
This sustainable vacation home is located in Kissimmee, Florida, just 13 minutes from Disney and 7.6 miles from Gatorland, making it a convenient base for exploring the area's attractions. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The five-bedroom, three-bathroom townhome provides ample space for families or groups of friends. Guests can enjoy a range of amenities, including a swimming pool, hot tub, bar, fitness centre, tennis court, and a garden, as well as family-friendly features like a kids' pool, an indoor play area, and a children's playground.
Viral One Of A Kind Lakeside 15b ~ Gated Resort ~ Theater ~ Pool & Spa By Disney - Kissimmee
9.0 14 reviews

Viral One Of A Kind Lakeside 15b ~ Gated Resort ~ Theater ~ Pool & Spa By Disney

apartment, Kissimmee
This spacious 15-bedroom villa, Viral Lakeside 15b@gated Resort|pool|theater|spa+, is situated in Kissimmee, Florida, within 2km of Shingle Creek Regional Park and Kissimmee Go-Karts, and 3km from Medieval Times and Capone's Dinner Show.
The 592 square metre property boasts 17 bathrooms, sleeps 38 guests, and includes a fitness centre, hot tub, garden, barbecue grills, and a fully equipped kitchen.
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