Compare Vacation Rentals & Airbnb in Kissimmee

15321 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Kissimmee vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

15321 Rentals and Airbnb in Kissimmee

Best family friendly Kissimmee vacation rentals

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

Bright, Immaculate, Private Pool, Gated Community - Kissimmee
9.7 56 reviews
Kissimmee
21/12 – 26/12
$459/nighttotal: $2295 (5 )

Bright, Immaculate, Private Pool, Gated Community

4 6
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.
Beautiful Spacious 3 Bedroom Villa With Private Pool And Wonderful Lake View - Kissimmee
8.6 99 reviews
Kissimmee
21/08 – 25/08
$287/nighttotal: $1148 (4 )

Beautiful Spacious 3 Bedroom Villa With Private Pool And Wonderful Lake View

3 4
house , Kissimmee
This Kissimmee villa enjoys a waterfront location, within 5km of Give Kids the World Village and 10km of Old Town, offering convenient access to attractions such as the 192 Flea Market and Shingle Creek Regional Park.
The 158 square metre property sleeps six guests in three bedrooms and two bathrooms, boasting a private pool, terrace, garden, free Wi-Fi, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
4 Bedroom 3 Bathroom Villas At Seven Dwarfs 10-102 - Kissimmee
9.5 4 reviews
Kissimmee
16/07 – 19/07
$365/nighttotal: $1095 (3 )

4 Bedroom 3 Bathroom Villas At Seven Dwarfs 10-102

4 8
house , Kissimmee
This spacious four-bedroom villa is situated near Seven Dwarfs in Kissimmee, Florida, approximately 11.3 kilometres from Disney Springs and Gatorland.
The 137 square metre property boasts three bathrooms, sleeps up to fifteen guests, and includes a private tennis court, swimming pool, fitness centre, and free Wi-Fi.
Family Getaway With Private Pool Close To Disney - Kissimmee
9.5 121 reviews
Kissimmee
15/07 – 27/08
$268/nighttotal: $11524 (43 )

Family Getaway With Private Pool Close To Disney

1 4
house , Kissimmee
This four-bedroom apartment is located in the Dharma Circle district of Kissimmee, just 14.5 kilometres from Disney, 17.4 kilometres from SeaWorld, and 22 kilometres from Universal Studios, making it an ideal base for exploring central Florida's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 146 square metre apartment is spacious and well-equipped, featuring a fully equipped kitchen, a formal dining area, and a family room with a flat-screen TV. Guests can enjoy a private screened-in pool, a communal beach-entry pool, a fitness centre, a games room, a walking trail, a kids' play area, and a covered lanai with outdoor furniture.

Best Kissimmee vacation rentals with parking

Club Wyndham Kingstown Reef - 1 Bedroom Suite - Kissimmee
Kissimmee
15/07 – 31/08
$495/nighttotal: $203940 (412 )

Club Wyndham Kingstown Reef - 1 Bedroom Suite

1 3
apartment , Williamsburg
This Williamsburg apartment, situated near Orlando's major theme parks and approximately 16 kilometres from Orlando International Airport, offers convenient access to popular attractions. This one-bedroom suite, boasting 79 square metres of floor space, comfortably accommodates four guests and includes a king bed, queen sleeper sofa, Wi-Fi, a balcony, and access to resort amenities such as swimming pools and a spa.
4bd Beautiful Escape W/ Pool & Bbq! - Kissimmee
9.6 27 reviews
Kissimmee
20/07 – 29/07
$262/nighttotal: $2358 (9 )

4bd Beautiful Escape W/ Pool & Bbq!

1 7
house , Kissimmee
This detached residence in the gated Le Reve Resort is situated in Kissimmee, offering excellent access to Walt Disney World Resort and Universal Studios Florida, with dining and shopping options nearby.
This family-friendly villa accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private swimming pool, a fully equipped kitchen, complimentary Wi-Fi, and on-site parking.
New Listing! Crystal Cove Resort, 6mi To Disney & 11mi To Universal - 71 - Kissimmee
8.9 68 reviews
Kissimmee
28/08 – 05/09
$366/nighttotal: $2928 (8 )

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

7 12
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.
4 Bedroom Townhouse At The Villas At Seven Dwarfs - Kissimmee
9.7 259 reviews
Kissimmee
31/10 – 07/11
$220/nighttotal: $1540 (7 )

4 Bedroom Townhouse At The Villas At Seven Dwarfs

4 2
apartment , Kissimmee
This four-bedroom townhouse is located in the Villas at Seven Dwarfs community in Kissimmee, just a short drive from theme parks, shopping malls, and outlet malls. The property has received excellent ratings for its location, cleanliness, and overall experience.
The townhouse comfortably sleeps eight guests and offers a range of amenities, including a swimming pool, jacuzzi, fitness centre, and a kids' playground. Guests can also enjoy the on-site bar, basketball court, and arcade, providing plenty of entertainment options for all ages.

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.

Destinations nearby

Best Kissimmee vacation rentals with a balcony

Chic Modern, Themed Bedrooms, Private Pool - Kissimmee
9.2 7 reviews
Kissimmee
02/07 – 05/07
$581/nighttotal: $1743 (3 )

Chic Modern, Themed Bedrooms, Private Pool

4 7
apartment , Kissimmee
This four-bedroom, three-bathroom Kissimmee townhouse, located in the Storey Lake Resort, is approximately 6.4 kilometres from Walt Disney World and offers easy access to other Orlando theme parks and local amenities.
The 223 square metre property sleeps up to 10 guests and boasts a private heated pool (heating payable separately), themed bedrooms (Wonder Woman and Star Wars), and access to Storey Lake Resort's lazy river, water slides, and other facilities, including a pirate-themed pool.
Two-story Resort Townhome With 4-pools  Minutes From Orlandos Top Attractions! - Kissimmee
8.8 3 reviews
Kissimmee
21/07 – 31/07
$202/nighttotal: $2020 (10 )

Two-story Resort Townhome With 4-pools Minutes From Orlandos Top Attractions!

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.
120 M² House ∙ 3 Bedrooms ∙ 8 Guests - Kissimmee
Kissimmee
02/07 – 31/07
$156/nighttotal: $4524 (29 )

120 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 1
house , Kissimmee
This three-bedroom Lakeside Reserve townhome in Kissimmee, Florida, offers convenient access to Walt Disney World, located just minutes away.
The 120 square metre property boasts a Mickey Mouse-themed bedroom, two king-size beds, a private pool, and accommodates up to eight guests, with amenities including a fitness centre and community playground.
Famous 5 Star Home In Kissimmee With Game Room - Kissimmee
10 2 reviews
Kissimmee
24/07 – 26/07
$697/nighttotal: $1394 (2 )

Famous 5 Star Home In Kissimmee With Game Room

5 6
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.

Best Kissimmee vacation rentals with air conditioning

153 M² Apartment ∙ 4 Bedrooms ∙ 11 Guests - Kissimmee
Kissimmee
01/07 – 07/07
$369/nighttotal: $2214 (6 )

153 M² Apartment ∙ 4 Bedrooms ∙ 11 Guests

4 11
apartment , Kissimmee
This Kissimmee holiday home, situated in the Summer Flowers community near US-192, is a short drive (approximately 16km) from Walt Disney World and Universal Studios Florida, with a Walmart Supercentre just 2 minutes away.
The 165 square metre property offers spacious accommodation for up to 11 guests, boasting 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen including a dishwasher, multiple Smart TVs, high-speed internet (up to 400 Mbps), and access to a community pool; complimentary baby equipment is also available.
All The Comforts Of Home! - Kissimmee
9.8 126 reviews
Kissimmee
01/08 – 06/08
$357/nighttotal: $1785 (5 )

All The Comforts Of Home!

4 4
house , Kissimmee
This four-bedroom, three-bathroom villa is situated in the city centre of Kissimmee, directly opposite the Terra Verde Resort's main clubhouse and a short drive from Walt Disney World® Resort, Reunion Resort Golf Course, and Disney Springs™.
This 152 square meter holiday home accommodates up to eight guests, boasting a private swimming pool with conservation views, a fully equipped kitchen with stainless steel appliances, and access to extensive resort amenities including a fitness centre, games room, and tennis court.
Dream Place Near The Magic Kingdom - Kissimmee
9.6 112 reviews
Kissimmee
05/11 – 08/11
$286/nighttotal: $858 (3 )

Dream Place Near The Magic Kingdom

1 6
house , Kissimmee
This Kissimmee townhouse enjoys a central location near US 192, offering easy access to Walt Disney World Resort (under 8 km away), Universal Orlando Resort (approximately 16 km), and SeaWorld Orlando (around 19 km).
The four-bedroom, two-bathroom property sleeps nine guests and boasts a private pool, Jacuzzi, and access to a gated community with further amenities including a gym and cinema; the fully equipped kitchen and in-unit laundry add convenience.
Cozy Townhome Near Orlando's Themeparks With Heated Communal Pool - Kissimmee
8.9 82 reviews
Kissimmee
27/06 – 04/07
$227/nighttotal: $1589 (7 )

Cozy Townhome Near Orlando's Themeparks With Heated Communal Pool

4 4
apartment , Kissimmee
This family-friendly holiday home is located in Kissimmee, within a mile of popular attractions like Kissimmee Go-Karts, 192 Flea Market, and Shingle Creek Regional Park. It has consistently received excellent ratings from previous guests. This spacious four-bedroom property provides ample space for families and groups. The house offers a range of amenities, including a private swimming pool, a Jacuzzi, a fitness centre, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
©2026 cozycozy.com