Holiday Rentals in Kissimmee

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Kissimmee holiday rentals
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Best Holiday rentals and Airbnb offers in Kissimmee

Discover Family-Friendly Self-Catering Rentals in Kissimmee

Getting the holiday rental right makes all the difference for a family trip to Kissimmee. Find city attractions within easy reach. Start comparing now.

Experience Kissimmee Living Near Vibrant Old Town - Kissimmee
9.4 54 reviews
Kissimmee
28/08 – 05/09
£182/nighttotal: Â£1456 (8 )

Experience Kissimmee Living Near Vibrant Old Town

6 12
house , Kissimmee
This six-bedroom Lake Berkley villa in Kissimmee, Florida is situated within 3.2 kilometres of Medieval Times Dinner & Tournament, the 192 Flea Market, and Shingle Creek Regional Park, and within 4.8 kilometres of Give Kids the World Village and Kissimmee Go-Karts.
The spacious property boasts a private pool, Jacuzzi, fitness centre, and tennis court, accommodating up to 12 guests with three bathrooms, a fully equipped kitchen, and free Wi-Fi; enjoy on-site amenities and nearby family attractions.
5br 5bath Pvt Home Bbq Pool 15min Disney 3056ft - Kissimmee
9.0 115 reviews
Kissimmee
05/11 – 08/11
£327/nighttotal: Â£981 (3 )

5br 5bath Pvt Home Bbq Pool 15min Disney 3056ft

5 6
house , Kissimmee
This spacious house is ideally located in Kissimmee, just 24 kilometres from Disney, 7.4 kilometres from Gatorland, and 16 kilometres from SeaWorld's Discovery Cove and Disney Springs. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This five-bedroom home comfortably accommodates large families or groups of friends. Guests can enjoy a private pool, patio, barbecue area, fitness room, fully equipped kitchen, hot tub, and outdoor dining area.
Spacious Condo W/ Pool,gym Near Disney & Seaworld - Kissimmee
9.7 23 reviews
Kissimmee
21/07 – 31/07
£103/nighttotal: Â£1030 (10 )

Spacious Condo W/ Pool,gym Near Disney & Seaworld

1 4
apartment , Kissimmee
This ground-floor apartment in the Club Cortile community, Kissimmee, Florida, enjoys excellent proximity to Walt Disney World Resort (9.2 km), SeaWorld Orlando (14 km), and Universal Orlando Resort (19.5 km).
The three-bedroom, two-bathroom property sleeps six, offering a king-size bed in the master suite, a queen bed in one guest room, and two single beds in another, plus amenities including a swimming pool, fitness centre, and children's play area within the community.
Elsa's Enchanting Escape Just 15 Minutes To Disney - Kissimmee
9.9 34 reviews
Kissimmee
27/06 – 04/07
£276/nighttotal: Â£1932 (7 )

Elsa's Enchanting Escape Just 15 Minutes To Disney

1 12
apartment , Kissimmee
This spacious six-bedroom, six-bathroom residence is located in a quiet Kissimmee neighbourhood, a convenient 24 kilometres from Walt Disney World.
This family-friendly holiday home offers accommodation for up to 14 guests, featuring a private pool and hot tub (additional cost applies), a games room with arcade, foosball, and ping pong, and a fenced garden with a barbecue.

Compare Holiday Rentals with Parking in Kissimmee

Free on-site parking comes with these holiday rentals in Kissimmee, allowing you to focus on the city centre from day one.

Family Vacation Resort Med Spa Nær Orlando Parks & International Airport. - Kissimmee
9.7 176 reviews
Kissimmee
17/08 – 24/08
£116/nighttotal: Â£812 (7 )

Family Vacation Resort Med Spa Nær Orlando Parks & International Airport.

3 3
resort , Kissimmee
This holiday home is conveniently located in Kissimmee, within a 5km radius of Medieval Times, 192 Flea Market, Give Kids the World Village, Shingle Creek Regional Park, and Kissimmee Go-Karts, making it easy to explore the area's attractions. Guests have consistently rated the property excellent for its location, cleanliness, and overall experience.
The three-bedroom property comfortably accommodates up to six guests. Enjoy a relaxing and fun-filled stay with on-site amenities like a water park, fitness centre, spa tub, swimming pool, and a fully equipped kitchen.
Budget & Pet Friendly Charming Family Suite - Kissimmee
Kissimmee
02/07 – 31/07
£61/nighttotal: Â£1769 (29 )

Budget & Pet Friendly Charming Family Suite

1 1
apartment , Kissimmee
This Kissimmee holiday apartment offers convenient access to major theme parks, with Old Town and Orlando Vineland Premium Outlets a short drive away.
The 30-square-metre (323-square-foot) self-catering flat features one bedroom, one bathroom, sleeps four guests, and includes a private balcony with pool views, a queen-size bed, and amenities such as a flat-screen TV, Wi-Fi, and on-site parking.
Free Early Check-in For Reservations Starting April: 13, 14, 15, 20, 21, 22, 27. - Kissimmee
10 107 reviews
Kissimmee
19/07 – 21/07
£210/nighttotal: Â£420 (2 )

Free Early Check-in For Reservations Starting April: 13, 14, 15, 20, 21, 22, 27.

3 2
apartment , Kissimmee
This modern townhouse is located in Kissimmee, within a gated community, just a short drive from Old Town and Disney Springs™, making it a convenient base for exploring the area’s attractions. The property has received excellent reviews from previous guests, highlighting its comfort and amenities.
This spacious home offers 135 square metres of living space and comfortably accommodates up to eight guests across three bedrooms and three bathrooms. The property features a fully equipped kitchen, a private patio, a swimming pool, a jacuzzi, and a range of entertainment options, including multiple smart TVs and a gaming console, ensuring a relaxing and enjoyable stay for all.
4 Bed 3 Bath Town-home With Pool Near Disney Townhouse - Kissimmee
9.3 613 reviews
Kissimmee
07/11 – 17/11
£258/nighttotal: Â£2580 (10 )

4 Bed 3 Bath Town-home With Pool Near Disney Townhouse

6 10
house , Kissimmee
This six-bedroom villa is located in Kissimmee, just 14 kilometres from Gatorland, Disney's Wide World of Sports, and Disney's Hollywood Studios. The property has received excellent ratings for location, user experience and cleanliness.
This spacious holiday home has a fully equipped kitchen, a private pool and patio, and a hot tub, fitness centre and children's playground. The villa also offers garden views, streaming services and a unique themed design.

Frequently asked questions about holiday rentals in Kissimmee

  • What should a first-time visitor not miss in Kissimmee?

    You've got to check out the theme parks, like Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando. They're a must-do for any first-timer in Kissimmee. And don't forget to visit the Kennedy Space Center Visitor Complex, it's a great place to learn about space exploration.
  • What are the best Airbnb and holiday rentals in Kissimmee?

  • 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.

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

    For a family-friendly vacation rental, the Reunion Resort area is a great option. It's close to all the theme parks and has lots of amenities like pools, restaurants, and golf courses. If you're looking for something more budget-friendly, the Celebration area is a good choice. It's a bit quieter and has a more community feel.
  • 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 top family-friendly attractions in Kissimmee?

    Kissimmee is a haven for families! You can't go wrong with the theme parks like Disney World, Universal Studios, and SeaWorld. For something a little different, head to Gatorland, where you can see alligators up close, or the Legoland Florida Resort, which is a great choice for younger kids.
  • What are the best holiday 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.

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

    The best time to book a vacation rental in Kissimmee is well in advance, especially if you're travelling during peak season, which is from June to August. You might get better deals if you book outside of these months, but availability might be limited.
  • 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 events or festivals should visitors check out in and around Kissimmee?

    Kissimmee has a vibrant events calendar! Check out the Osceola County Fair in February, the Epcot International Food & Wine Festival in the autumn, or the Kissimmee Air & Space Show in April. For something unique, head to the Osceola Heritage Park for the annual Chili Cook-Off.
  • 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.

  • What are the best budget-friendly activities in Kissimmee?

    For a budget-friendly day out, head to the Kissimmee Lakefront Park, where you can enjoy a picnic by the lake, go for a walk or bike ride, or even rent a paddleboat. Another great option is the Paddling Center at Shingle Creek, where you can enjoy a scenic kayak or canoe trip.
  • What are the best walking or cycling routes in Kissimmee?

    The East Lake Tohopekaliga Loop Trail is a popular choice for walking and cycling. It's a 10 km loop around East Lake Tohopekaliga, offering beautiful views of the lake and surrounding nature. For a shorter route, try the Celebration Town Center Trail, which is a paved trail that winds through the charming town of Celebration.
  • Are there pet-friendly attractions in Kissimmee?

    Absolutely! Many of the parks and attractions in Kissimmee are pet-friendly, including the Kissimmee Lakefront Park, the Celebration Town Center, and the Osceola Heritage Park. You can even take your furry friend to the Kennedy Space Center Visitor Complex, as long as they're on a leash.
  • What are the benefits of choosing a vacation rental in Kissimmee?

    Vacation rentals in Kissimmee offer more space and privacy compared to hotels, often with amenities like private pools and kitchens. They can also be more budget-friendly, especially for larger groups or families. Plus, you'll have the flexibility to cook your own meals and enjoy your own space.
  • What are the top sports attractions and facilities in Kissimmee?

    Kissimmee is a haven for sports lovers! The ESPN Wide World of Sports Complex is a major draw, hosting a variety of sporting events throughout the year. You can also find several golf courses, including the Reunion Resort Golf Courses, and the Kissimmee Sports Complex, which has facilities for baseball, soccer, and other sports.

Destinations nearby

Check Out Holiday Rentals with a Balcony in Kissimmee

Private balconies with city skyline views come as standard at these holiday rentals in Kissimmee for a lovely start to your day.

4-bed Resortw/pool, And Dualmasters - Kissimmee
10 1 review
Kissimmee
22/07 – 02/08
£124/nighttotal: Â£1364 (11 )

4-bed Resortw/pool, And Dualmasters

4 7
apartment , Kissimmee
This spacious four-bedroom, two-bathroom holiday home is situated within the Lake Berkley Resort in Kissimmee, Florida, offering a convenient base just 1.6 to 2.4 kilometres from Walt Disney World Resort and a short drive from Universal Studios and SeaWorld.
This 182 square metre residence accommodates up to eight guests with a three-way split bedroom layout for privacy, featuring a private pool and spa, a fully equipped kitchen, a garage game room, and access to the resort's extensive amenities including a clubhouse, fitness centre, and lakefront beach.
2929 Ss - Disney Delight: 4br Pool Near Parks - Kissimmee
9.6 68 reviews
Kissimmee
17/07 – 19/07
£280/nighttotal: Â£560 (2 )

2929 Ss - Disney Delight: 4br Pool Near Parks

4 3
house , Kissimmee
This Kissimmee villa is ideally situated approximately 12-14km from Gatorland, Disney Springs, and various Disney parks, offering easy access to major attractions.
The four-bedroom, three-bathroom property sleeps a large family group, boasting a private pool, free Wi-Fi, a fully equipped kitchen with dishwasher, and a balcony; nearby amenities include a fitness centre, tennis court and spa.
New And Amazing Tiny House In Kissimmee, Fl Only 20 Minutes To Disney/universal - Kissimmee
Kissimmee
26/07 – 30/07
£90/nighttotal: Â£360 (4 )

New And Amazing Tiny House In Kissimmee, Fl Only 20 Minutes To Disney/universal

1 2
resort , Kissimmee
This Kissimmee resort, "New And Amazing Tiny House In Kissimmee, FL Only 20 Minutes To Disney/Universal", is situated approximately 32 kilometres from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando.
The self-catering property features one bedroom, one bathroom, sleeps four guests, and includes a swimming pool, terrace, garden, and free Wi-Fi; nearby amenities include a fitness room and playground.
Storey Lake Resort 6 Bedroom Private Pool Home With Game Room - Kissimmee
9.3 30 reviews
Kissimmee
28/08 – 05/09
£281/nighttotal: Â£2248 (8 )

Storey Lake Resort 6 Bedroom Private Pool Home With Game Room

6 12
resort , Kissimmee
Storey Lake Resort's six-bedroom house, near Shingle Creek Regional Park and Capone's Dinner Show (both within 1.6km), offers a convenient Kissimmee location close to Kissimmee Go-Karts and Lake Buena Vista Factory Stores (both within 4.8km).
This self-catering holiday home sleeps 13 guests and boasts a private pool, games room, spa tub, and free Wi-Fi; on-site water park entertainment is also available.

Best Kissimmee holiday rentals with air conditioning

7 Miles From Disney World - Kissimmee
9.4 65 reviews
Kissimmee
21/08 – 24/08
£96/nighttotal: Â£288 (3 )

7 Miles From Disney World

3 1
apartment , Kissimmee
This three-bedroom townhouse is located just 11 kilometres from Walt Disney World in Kissimmee, Florida, providing easy access to the area's major theme parks. It has received excellent user ratings for its comfort and amenities.
The property spans 136 square metres and comfortably accommodates up to seven guests. It features a fully equipped kitchen, a garden, a swimming pool, and a gated community with tennis courts and a clubhouse with a small gym.
Cozy Studio In Kissimmee - Kissimmee
10 1 review
Kissimmee
26/07 – 30/07
£65/nighttotal: Â£260 (4 )

Cozy Studio In Kissimmee

1 2
studio , Kissimmee
This self-contained studio apartment is situated in the Windward Cay neighbourhood of Kissimmee, Florida, approximately 24 kilometres from Walt Disney World Resort.
The 1-bedroom, 1-bathroom apartment sleeps two guests and features a fully equipped kitchen, high-speed Wi-Fi, a Roku TV with Netflix and Hulu access, and is conveniently located for access to other attractions including Disney's Hollywood Studios and Epcot.
Lakeview Home In Terra Verde:pool&resort Perks - Kissimmee
9.3 11 reviews
Kissimmee
15/07 – 27/08
£74/nighttotal: Â£3182 (43 )

Lakeview Home In Terra Verde:pool&resort Perks

1 4
apartment , Kissimmee
Lakeview Home In Terra Verde:pool&resort Perks is situated in the Terra Verde Resort, Kissimmee, Florida, offering easy access to Walt Disney World, Universal Studios Florida, and SeaWorld, all within a 24-48 km radius.
This three-bedroom, three-bathroom holiday home sleeps six guests and boasts a fully equipped kitchen, private outdoor seating with a grill, and access to resort amenities including a heated pool, hot tub, mini-golf, fitness centre, and playground.
Lovely Private Pool Villa Wfree Resort Access - Kissimmee
9.4 55 reviews
Kissimmee
26/06 – 27/06
£861/nightfor 1 night

Lovely Private Pool Villa Wfree Resort Access

6 15
house , Kissimmee
This Kissimmee villa, located approximately 11 kilometres from Disney Springs and Disney's Hollywood Studios, offers easy access to major theme parks and attractions such as Gatorland (11 kilometres) and SeaWorld's Discovery Cove (14 kilometres).
This six-bedroom, five-bathroom property boasts 311 square metres of living space, a private pool, and access to resort amenities including a restaurant, bar, fitness centre, and children's playground; perfect for large families or groups.
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