Holiday Rentals in Kissimmee

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Kissimmee holiday rentals
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Best Holiday rentals and Airbnb offers in Kissimmee

Search Holiday Rentals near the Heart of the City in Kissimmee

Coordinate an unforgettable urban break using private, independent holiday rentals for couples situated close to vibrant Kissimmee landmarks.

3120-206dr Storey Lake, Condo 2/2 Garden View - Kissimmee
9.1 175 reviews

3120-206dr Storey Lake, Condo 2/2 Garden View

apartment, Kissimmee
This apartment is ideally situated in Kissimmee, just a short drive from popular attractions like Gatorland and Florida Mall, making it a convenient base for exploring the area. It consistently receives excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom apartment offers 111 square metres of space, comfortably accommodating up to seven guests. Enjoy a range of amenities including a fully equipped kitchen, a swimming pool, a fitness centre, and a restaurant, ensuring a comfortable and enjoyable stay.
Super Boho - At Lake Toho Fishing Vintage Vibes - Kissimmee
10 2 reviews

Super Boho - At Lake Toho Fishing Vintage Vibes

house, Kissimmee
This two-bedroom Kissimmee holiday home is located less than 0.8km from the city centre and under 8km from Gatorland, with SeaWorld and Disney Springs within a 21km radius.
The 71 square metre property offers a spacious layout sleeping up to six guests, boasting a fully equipped kitchen with modern appliances, air conditioning, Wi-Fi, and pet-friendly accommodation.
Disney Townhouse With Themed Room - Kissimmee
8.5 47 reviews

Disney Townhouse With Themed Room

house, Kissimmee
This Disney Townhouse is situated in Kissimmee, just a short drive from popular attractions like Gatorland, SeaWorld Orlando, and Disney Springs. The house has received excellent ratings for location, cleanliness and overall satisfaction.
This four-bedroom property features a fully-equipped kitchen, air conditioning, and a private pool. Guests can enjoy free Wi-Fi, on-site parking, and themed rooms for a truly magical experience.
Super Boho @ Lake Toho | Fishing | Sleeps 6 | - Kissimmee
9.8 114 reviews

Super Boho @ Lake Toho | Fishing | Sleeps 6 |

apartment, Kissimmee
This historic Kissimmee townhome, renovated in a vintage boho style, is located in Downtown Kissimmee, a short walk from Lake Toho and opposite a park, offering easy access to major attractions such as Walt Disney World Resort (13-24km away) and Universal Orlando Resort (37km away).
Sleeping up to seven guests, this two-bedroom, one-bathroom property boasts a king-size bed and two double beds, a fully equipped kitchen with microwave and dishwasher, air conditioning, a garden, parking, and starter supplies; optional car rental and transportation services are available.

Best Kissimmee holiday rentals with air conditioning

Modern 3 Bedroom Townhouse With A Pool! - Kissimmee
9.2 16 reviews

Modern 3 Bedroom Townhouse With A Pool!

apartment, Kissimmee
This three-bedroom, two-bathroom apartment in Kissimmee offers a luxurious poolside retreat within a gated community, conveniently situated 3.2 to 4 kilometres from Walt Disney World® Resort and Universal Orlando Resort.
This contemporary holiday let, accommodating up to six guests, features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, air conditioning, and Wi-Fi, making it an ideal base for exploring nearby attractions like Old Town and numerous golf courses.
Stay 15 Minutes From Disney! - Kissimmee
9.5 164 reviews

Stay 15 Minutes From Disney!

house, Kissimmee
This three-bedroom townhouse is situated within the gated Terra Verde Resort, conveniently located just a short distance from the popular theme parks and attractions of Kissimmee. The property offers a fully equipped kitchen, a private swimming pool, and access to the resort's fitness centre and other amenities, making it ideal for families or groups of up to six guests.
4 Bedrooms 4 Bathrooms Bella Vida 440 Lf - Kissimmee
9.5 151 reviews

4 Bedrooms 4 Bathrooms Bella Vida 440 Lf

house, Kissimmee
This four-bedroom property is located in Kissimmee, just under ten miles from Disney's Hollywood Studios and Disney's Wide World of Sports, making it ideal for families or groups wanting to explore the area's attractions. The house has received excellent ratings for location, cleanliness and overall user experience.
The 177 square metre house offers ample space for a comfortable stay. The property boasts a range of amenities including a swimming pool, spa, fitness centre, and a fully equipped kitchen with a dishwasher, making it perfect for relaxing and entertaining.
Disney Area | Resort Pool | Gated Townhome - Kissimmee
10 9 reviews

Disney Area | Resort Pool | Gated Townhome

apartment, Kissimmee
This three-bedroom, two-and-a-half-bathroom townhome in Kissimmee, Florida, is situated near US-192, approximately 16-24 km from Walt Disney World Resort and 48 km from Universal Orlando Resort.
The property, part of the Terra Verde Resort, offers a private screened patio, a fully equipped kitchen, in-unit laundry, and access to a swimming pool, jacuzzi, fitness centre, and mini-golf; sleeping six guests comfortably.

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.

Popular destinations

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.

Marvelous 4bd W Pool Close To Disney At Storey Lake 2629 - Kissimmee
No reviews

Marvelous 4bd W Pool Close To Disney At Storey Lake 2629

house, Kissimmee
Holiday house to rent. This accommodation is based in Kissimmee.
Services and facilities include a dish washer, a spa and an iron. Take advantage of the Free Parking with this accommodation.
Roomy House Near Disney With Resort Pool And Patio Bbq - Kissimmee
8.7 53 reviews

Roomy House Near Disney With Resort Pool And Patio Bbq

apartment, Kissimmee
This three-bedroom Kissimmee townhouse, situated 13 kilometres from Gatorland and 16 kilometres from Disney Springs and Disney's Wide World of Sports, offers convenient access to major attractions.
The 139 square metre property boasts three bathrooms, sleeps thirteen guests, and includes a private patio with lake views, a fully equipped kitchen, and access to an on-site swimming pool, fitness centre, spa, and restaurant.
Beautiful Lake View Golf Home 2723 - Kissimmee
9.5 104 reviews

Beautiful Lake View Golf Home 2723

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.
Kissimmee Retreat W/ Pool: Near Disney & Golf! - Kissimmee
9.0 242 reviews

Kissimmee Retreat W/ Pool: Near Disney & Golf!

house, Kissimmee
This Kissimmee vacation home is conveniently located just 7.1 miles from Gatorland and 12 miles from the Florida Mall, offering easy access to popular attractions. The property has received excellent ratings from previous guests for its cleanliness, location and overall experience.
The three-bedroom property spans 175 square metres and comfortably accommodates up to six guests. Enjoy a refreshing dip in the private pool, relax in the spa, or play a game of tennis on the court.

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.

Kissimmee's Hidden Gem - Kissimmee
9.9 72 reviews

Kissimmee's Hidden Gem

apartment, Kissimmee
This four-bedroom, two-bathroom holiday home in Kissimmee is situated approximately 32 kilometres from the Walt Disney World Resort and Universal Orlando Resort, with convenient access to Fun Spot America and the Celebration district.
This family-friendly apartment accommodates up to 10 guests and boasts a private heated pool, a games room with pool and ping pong tables, a jacuzzi tub, and essential baby gear, all within easy reach of local dining options.
Bright Open-concept Home | Pool And Jacuzzi! - Kissimmee
9.5 144 reviews

Bright Open-concept Home | Pool And Jacuzzi!

house, Kissimmee
This four-bedroom apartment is situated in Kissimmee, just 8km from Disney, 11km from SeaWorld and a 40-minute drive from Universal Studios. The apartment has received excellent ratings for location, cleanliness, and user experience.
The spacious property can accommodate up to eight guests and offers a fully equipped kitchen, a private pool, and a host of amenities including a fitness centre, a games room, and a children's play area. Guests can also enjoy the benefits of a gated community with a lake, lounge, jacuzzi, walking trail, and sports courts.
Special Rates Available In Sep And  Oct Of 2026 - Kissimmee
9.4 138 reviews

Special Rates Available In Sep And Oct Of 2026

house, Kissimmee
This four-bedroom, three-bathroom villa is situated in the Terra Verde Resort community in Kissimmee, Florida, offering convenient access to Walt Disney World Resort, Disney's Hollywood Studios, and Epcot, all within a short driving distance.
The 149 square metre (1600 square foot) property boasts a private swimming pool, jacuzzi, and tennis court, sleeping up to eight guests and including a fully equipped kitchen; a $25 resort fee applies.
24/7 Gated 6 /3.5 Bath Off 192,pool, Tennis 1073 - Kissimmee
10 62 reviews

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

apartment, Kissimmee
This six-bedroom, three-bathroom villa is situated in a gated community in Kissimmee, Florida, a short distance from US-192, offering easy access to Walt Disney World and other attractions.
Sleeping fourteen comfortably, this spacious property boasts a private pool, themed children's bedrooms (Marvel and Mickey Mouse), a games room, and modern amenities including stainless steel appliances and TVs in all bedrooms, plus nearby tennis courts and a community water feature.

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.

Disney Pool Paradise | Sleeps 8 | Family Fun - Kissimmee
9.7 81 reviews

Disney Pool Paradise | Sleeps 8 | Family Fun

apartment, Kissimmee
Cc2309cc: Gym, Pool, Hot Tub - 8 Guests - Resort Style - Kissimmee
8.7 20 reviews

Cc2309cc: Gym, Pool, Hot Tub - 8 Guests - Resort Style

apartment, Kissimmee
9 Mi To Disney: Resort Getaway W/ Private Patio! - Kissimmee
10 3 reviews

9 Mi To Disney: Resort Getaway W/ Private Patio!

house, Kissimmee
Veranda Palms Luxurious Home W/pool & Near Disney - Kissimmee
9.7 257 reviews

Veranda Palms Luxurious Home W/pool & Near Disney

house, Kissimmee

Explore 5-Star Self-Catering Rentals in Kissimmee

Upscale holiday rentals in Kissimmee offer a refined stay you will want to return to. Enjoy premium amenities and attentive service.

3bd 2ba Luxe Villa Located 20 Minutes From Disney - Kissimmee
9.6 114 reviews

3bd 2ba Luxe Villa Located 20 Minutes From Disney

house, Kissimmee

Top Pet-Friendly Holiday Rentals in Kissimmee

These dog-friendly holiday rentals in Kissimmee feature city walks on the doorstep. Your dog will love the trip as much as you do.

Luxury 4 Bedroom 3 Bath Pool Home 283 - Kissimmee
No reviews

Luxury 4 Bedroom 3 Bath Pool Home 283

house, Kissimmee
Spacious 1 Bedroom House In Disney Area 5 Star Rated Mill Creek Resort 2753 - Kissimmee
9.0 4 reviews

Spacious 1 Bedroom House In Disney Area 5 Star Rated Mill Creek Resort 2753

apartment, Kissimmee
Waterfront/kayakfishing/neardisney&laketohoa/pets - Kissimmee
9.2 15 reviews

Waterfront/kayakfishing/neardisney&laketohoa/pets

house, Kissimmee
Convenient Private Annex - Kissimmee
10 11 reviews

Convenient Private Annex

house, Kissimmee

Choose the Right Holiday Rentals with a Pool in Kissimmee

These holiday rentals and Airbnbs in Kissimmee include a pool, so a proper swim in the heart of the city is always on the cards.

1192sbc South Beach Villa - Kissimmee
9.5 131 reviews

1192sbc South Beach Villa

house, Kissimmee
Lovely Remodeled 1 Bed, 1 Bath Condo,  Just Miles From Disney! Great Location. - Kissimmee
9.4 91 reviews

Lovely Remodeled 1 Bed, 1 Bath Condo, Just Miles From Disney! Great Location.

apartment, Kissimmee
5br/5ba Game/pool Villa 9 Miles To Disney - Kissimmee
9.4 48 reviews

5br/5ba Game/pool Villa 9 Miles To Disney

house, Kissimmee
Modern 3br Townhouse | Near Disney | Resort Pool - Kissimmee
9.8 124 reviews

Modern 3br Townhouse | Near Disney | Resort Pool

house, Kissimmee

Guest-Favourite Holiday Rentals with a Hot Tub in Kissimmee

Whether you prefer a jacuzzi or a hot tub, these holiday rentals in Kissimmee include one for your private use. See what catches your eye now.

Wonderful Terra Verde Orlando Vacation Home - Kissimmee
8.0 14 reviews

Wonderful Terra Verde Orlando Vacation Home

house, Kissimmee
Mi Casita Near Disney & Universal - Kissimmee
9.7 138 reviews

Mi Casita Near Disney & Universal

apartment, Kissimmee
Orlando, Kissimmee, Town Home - Kissimmee
9.5 101 reviews

Orlando, Kissimmee, Town Home

apartment, Kissimmee
3br Pool Townhome Near Disney - Kissimmee
9.8 74 reviews

3br Pool Townhome Near Disney

apartment, Kissimmee
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