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.

8br Pool & Arcade – Enchanted Escape Retreat - Kissimmee
9.8 34 reviews
Kissimmee
10/07 – 24/07
£300/nighttotal: £4200 (14 )

8br Pool & Arcade – Enchanted Escape Retreat

8 15
house , Kissimmee
This eight-bedroom house is situated in the Sonoma Resort community in Kissimmee, Florida, a short distance (approximately 1-2 km) from Walt Disney World and numerous restaurants and shops.
The property boasts a spacious layout, sleeping up to 16 guests, and includes a large kitchen with dual refrigerators and dishwashers, a private pool and spa, a games room, a gas BBQ, and access to resort amenities such as a fitness centre.
Free Resort Access, Private Pool Near Disney 2966 - Kissimmee
9.6 111 reviews
Kissimmee
04/07 – 18/07
£234/nighttotal: £3276 (14 )

Free Resort Access, Private Pool Near Disney 2966

4 4
house , Kissimmee
This four-bedroom house is located in Kissimmee, just 13 kilometres from Gatorland and 13 kilometres from Disney Springs.
The 178 square metre property offers a private pool, a Jacuzzi, a bar and a fitness centre, perfect for families or groups of friends.
Friendly 4bd Close To Disney @ Storey Lake 2629 - Kissimmee
9.6 5 reviews
Kissimmee
25/12 – 03/01
£307/nighttotal: £2763 (9 )

Friendly 4bd Close To Disney @ Storey Lake 2629

4 11
apartment , Kissimmee
This spacious Kissimmee holiday home, located within the Storey Lake Resort, offers convenient access to major highways, placing Walt Disney World and Universal Studios within easy reach.
The 186 square metre (1999 square foot) property boasts four bedrooms, three bathrooms, sleeps up to twelve guests, and includes a private terrace, swimming pool, jacuzzi, and access to resort amenities such as a lazy river and fitness centre.
5-star Gem In Kissimmee With Game Room - Kissimmee
10 2 reviews
Kissimmee
02/07 – 05/07
£351/nighttotal: £1053 (3 )

5-star Gem In Kissimmee With Game Room

5 10
apartment , Kissimmee
This five-bedroom, four-bathroom holiday home in Kissimmee's Cumbrian Lakes district is conveniently located 8 minutes' drive from Give Kids the World Village and 5 minutes' drive from Green Meadows Petting Farm, with Walt Disney World® Resort also in close proximity.
This family-friendly apartment accommodates up to 14 guests and features a heated swimming pool, garden, table tennis, billiards, and a well-equipped kitchen, with a ski area and kayak available for outdoor pursuits.

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 Getaway Townhome At Lake Berkley 15min To Disney - Kissimmee
9.0 42 reviews
Kissimmee
20/11 – 29/11
£141/nighttotal: £1269 (9 )

Family Getaway Townhome At Lake Berkley 15min To Disney

3 2
house , Kissimmee
This three-bedroom townhouse is situated in Kissimmee, just a short drive from Disney's Wide World of Sports and a 15-minute journey to Disney World, making it an ideal base for exploring the area's attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The townhouse offers ample space for families or groups of friends, and features a private patio for outdoor relaxation. You can also enjoy a range of amenities including a swimming pool, a fitness room, and a children's playground, ensuring there's something for everyone to enjoy.
***Big Disney Family Home!*** Sleeps 12!  Private Pool, Spa And Game Room! - Kissimmee
9.8 239 reviews
Kissimmee
31/07 – 03/08
£297/nighttotal: £891 (3 )

***Big Disney Family Home!*** Sleeps 12! Private Pool, Spa And Game Room!

4 9
apartment , Kissimmee
This Kissimmee holiday home, situated in a gated community 8km from Walt Disney World and 24km from Universal Orlando Resort, offers convenient access to central Florida's major attractions.
The 186-square-metre property boasts four bedrooms, four bathrooms, sleeps twelve guests, and includes a private heated pool and hot tub, a games room, and access to a community clubhouse with further amenities.
Wyndham Star Island - 1 Bedroom Suite - Kissimmee
10 1 review
Kissimmee
15/07 – 31/08
£140/nighttotal: £57680 (412 )

Wyndham Star Island - 1 Bedroom Suite

1 3
apartment , Kissimmee
This Kissimmee condo, approximately 20 kilometres from Orlando International Airport, offers convenient access to Walt Disney World® Resort, Old Town, and ESPN Wide World of Sports.
The 44-square-metre one-bedroom suite sleeps four, featuring two double beds, a queen sleeper sofa, a fully equipped kitchen with microwave and dishwasher, plus a terrace, swimming pool, and parking; Wi-Fi is available for a daily fee.
Newly Renovated Home With 4 Bedrooms In Which 2 Are Masters And A Heated Pool - Kissimmee
9.3 223 reviews
Kissimmee
26/07 – 30/07
£225/nighttotal: £900 (4 )

Newly Renovated Home With 4 Bedrooms In Which 2 Are Masters And A Heated Pool

4 8
apartment , Kissimmee
This Kissimmee holiday home is ideally situated within 3km of Give Kids the World Village and Shingle Creek Regional Park, offering easy access to family attractions and the 192 Flea Market.
Sleeping up to 12 guests, this four-bedroom, three-bathroom property boasts a private pool, jacuzzi, sauna, fitness centre and barbecue facilities, alongside a fully equipped kitchen and free Wi-Fi.

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.

Stunning 3bd Condo 14 Mins To Disney World L Gated - Kissimmee
10 3 reviews
Kissimmee
04/07 – 01/08
£102/nighttotal: £2856 (28 )

Stunning 3bd Condo 14 Mins To Disney World L Gated

3 4
apartment , Kissimmee
This three-bedroom Kissimmee apartment, ideal for families, is situated less than 1.1 kilometres from Capone's Dinner Show and within 4.8 kilometres of Medieval Times and the 192 Flea Market.
The self-catering property boasts a fully equipped kitchen, two bathrooms, a private balcony, free Wi-Fi, and access to a swimming pool and fitness centre; sleeping up to six guests.
Beautiful Home Near Disney Private Poolbbq Downtown - Kissimmee
9.8 49 reviews
Kissimmee
24/07 – 26/07
£335/nighttotal: £670 (2 )

Beautiful Home Near Disney Private Poolbbq Downtown

4 6
apartment , Kissimmee
This four-bedroom, two-bathroom holiday home is situated in Historic Downtown Kissimmee, offering convenient walking access to Kissimmee Lakefront Park and being within 13-23km of various Disney parks.
Sleeping up to ten guests, the property boasts a private enclosed pool and jacuzzi, a pool table, and a terrace, all within easy reach of local restaurants, shopping, and nightlife.
New Themed 10b Villa|pool|spa - Kissimmee
9.4 12 reviews
Kissimmee
24/07 – 29/07
£588/nighttotal: £2940 (5 )

New Themed 10b Villa|pool|spa

10 25
house , Kissimmee
This luxurious ten-bedroom villa in Kissimmee, Florida, boasts a waterfront location within 5km of Shingle Creek Regional Park, Kissimmee Go-Karts, and the 192 Flea Market.
The 418-square-metre property offers a private pool, jacuzzi, spa, tennis court, and concierge services, accommodating up to 25 guests with five bathrooms and a fully equipped kitchen; onsite amenities include a water park and game room.
3br Resort Townhome 4mi Disney | Pools, Arcade - Kissimmee
8.8 3 reviews
Kissimmee
21/07 – 31/07
£108/nighttotal: £1080 (10 )

3br Resort Townhome 4mi Disney | Pools, Arcade

3 4
apartment , Kissimmee
This three-bedroom Kissimmee townhome, part of the ‘Two-story Resort Townhome With 4-pools – Minutes From Orlando’s Top Attractions!’ offer in the Venetian Bay Villages community, is less than 1.6km from Shingle Creek Regional Park and within 4.8km of Give Kids the World Village.
The 121-square-metre property boasts a private pool, a balcony, free WiFi, and a fully equipped kitchen, sleeping up to six guests and offering access to on-site amenities including a fitness centre, tennis court, and multiple swimming pools.

Best Kissimmee holiday rentals with air conditioning

161 Castaway Villa 4 Bed Pool&spa Resort - Kissimmee
9.0 5 reviews
Kissimmee
18/09 – 20/09
£199/nighttotal: £398 (2 )

161 Castaway Villa 4 Bed Pool&spa Resort

4 8
house , Kissimmee
This Kissimmee holiday home, situated 13.2 km from Gatorland, 16 km from Disney Springs and Disney's Wide World of Sports, and 22.5 km from Orlando International Airport, offers convenient access to major attractions.
This 1000 square metre property boasts four bedrooms, three bathrooms, sleeps fifteen guests, and includes a private pool, spa, fully equipped kitchen, free Wi-Fi, and free private parking.
Casa Bonita - Kissimmee
10 54 reviews
Kissimmee
23/07 – 26/07
£64/nighttotal: £192 (3 )

Casa Bonita

1 2
cabin , Kissimmee
This romantic tiny home is situated in a quiet Kissimmee neighbourhood, a short distance (within a few kilometres) of Walt Disney World Resort, Universal Orlando Resort's Epic Universe, SeaWorld Orlando, and Volcano Bay.
This self-catering cottage offers a compact yet fully equipped kitchen, one bedroom, one bathroom, and sleeps two guests, boasting a comfy full-size bed and a relaxing outdoor patio area.
Magical Memories! Splash Pad/pool Resort! - Kissimmee
9.8 8 reviews
Kissimmee
03/07 – 05/07
£184/nighttotal: £368 (2 )

Magical Memories! Splash Pad/pool Resort!

3 5
house , Kissimmee
This townhome in Kissimmee offers excellent access to Walt Disney World, SeaWorld, and Universal Studios, all within a short drive.
The 121 square meter property sleeps six across three bedrooms and two bathrooms, featuring a fully equipped kitchen, private patio, on-site laundry, and access to a resort with a pool and hot tub.
South Facing Pool, Close To Attractions, Remodeled - Kissimmee
9.5 42 reviews
Kissimmee
01/01 – 08/01
£216/nighttotal: £1512 (7 )

South Facing Pool, Close To Attractions, Remodeled

4 2
house , Kissimmee
This Kissimmee holiday home is ideally situated approximately 11.6km from Gatorland and within a 14.5-16km radius of major Disney attractions including Disney Springs, Disney's Wide World of Sports, Disney's Boardwalk and Disney's Hollywood Studios.
The 167 square metre property boasts four bedrooms, three bathrooms (including a hot tub), a private pool, spa, and fully equipped kitchen; free Wi-Fi and parking are also provided.
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