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Kissimmee, FL villas
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8901 Villa rentals in Kissimmee, FL

Choose the Right Holiday Houses with Swimming Pool in Kissimmee, FL

Having a pool at your vacation home in Kissimmee, FL lets you enjoy a proper swim in the city without any extra planning.

Harry Potter Lives Here! Unforgettable Home, Pool, Sleeps 8, Near Dis, Low Rates! - Kissimmee, FL
10 2 reviews
Kissimmee, FL
07/03 – 07/05
$284/nighttotal: $568 (2 )

Harry Potter Lives Here! Unforgettable Home, Pool, Sleeps 8, Near Dis, Low Rates!

3 7
house , Kissimmee
This Kissimmee vacation home, located approximately 7-8 miles from Disney's Wide World of Sports, Hollywood Studios, and Blizzard Beach, offers easy access to major Disney attractions. This 1500-square-foot property boasts three bedrooms, two bathrooms, sleeps up to fifteen guests, and includes a private pool, hot tub, fitness center, tennis court, and full-day security.
Luxurious 4 Bedroom/3.5 Bathroom Home, Perfectly Located With Private Conservation View Pool & Game Room - Kissimmee, FL
9.6 55 reviews
Kissimmee, FL
07/26 – 07/30
$314/nighttotal: $1256 (4 )

Luxurious 4 Bedroom/3.5 Bathroom Home, Perfectly Located With Private Conservation View Pool & Game Room

4 8
house , Kissimmee
This family-friendly Kissimmee villa is centrally located, within two miles of Medieval Times, the 192 Flea Market, and Capone's Dinner Show, and 2.5 miles from Give Kids the World Village.
This 1960-square-foot vacation home boasts four bedrooms, a private pool, a game room, and access to an on-site water park, offering ample space and entertainment for families or groups.
Storey Lake Townhome | Private Pool | Disney - Kissimmee, FL
9.8 69 reviews
Kissimmee, FL
07/03 – 07/05
$433/nighttotal: $866 (2 )

Storey Lake Townhome | Private Pool | Disney

1 7
house , Kissimmee
This Kissimmee vacation home is located in a modern resort-style community near major attractions and shopping malls, offering convenient access to Kissimmee's offerings. This four-bedroom, three-bathroom house sleeps up to 11 guests and boasts a private pool, fitness center, and driveway parking for 3-4 cars, plus all the comforts of home.
Private Tiny Home For Your Vaca! - Kissimmee, FL
9.8 83 reviews
Kissimmee, FL
08/04 – 08/18
$81/nighttotal: $1134 (14 )

Private Tiny Home For Your Vaca!

1 2
cabin , Kissimmee
This Kissimmee vacation home, ideally located near major theme parks, likely offers easy access to attractions like Walt Disney World and Universal Orlando Resort, potentially within a 10-20 minute drive.
This one-bedroom, one-bathroom rental boasts a full kitchen, in-unit laundry, and a private pool, comfortably accommodating up to four guests and offering a fitness center for added convenience.

Best family friendly Kissimmee, FL villas and beach houses

Among the 8901 accommodations in Kissimmee, FL, here are the 4 best family friendly villas and beach houses

Free Resort Access, Private Pool Near Disney 2966 - Kissimmee, FL
9.6 111 reviews
Kissimmee, FL
07/24 – 07/31
$210/nighttotal: $1470 (7 )

Free Resort Access, Private Pool Near Disney 2966

1 3
house , Kissimmee
This 4-bedroom vacation home is situated in Kissimmee, just 8 miles from Gatorland and 8.3 miles from Disney Springs.
The 1,920-square-foot house features a private pool, a fully equipped kitchen, a bar, a fitness center, and free private parking.
Disney Townhome - Kissimmee, FL
9.4 309 reviews
Kissimmee, FL
06/26 – 06/28
$200/nighttotal: $400 (2 )

Disney Townhome

1 6
house , Kissimmee
This Kissimmee vacation home is ideally located in a gated community, just 8 miles from Walt Disney World and 11 miles from Universal Studios Florida and Islands of Adventure.
The 3-bedroom, 2-bathroom house sleeps 8 guests and boasts a private pool, patio, full kitchen with dishwasher, and free parking in a secure community, offering easy access to area restaurants and attractions.
Near Disney! Private Pool/themed Kids Br/storey Lake 20051 - Kissimmee, FL
Kissimmee, FL
07/13 – 07/17
$492/nighttotal: $1968 (4 )

Near Disney! Private Pool/themed Kids Br/storey Lake 20051

6 15
house , Kissimmee
This 6-bedroom, 5-bathroom villa in Kissimmee's Storey Lake community is 8 miles from Walt Disney World, 8 miles from SeaWorld Orlando, and 12 miles from Universal Orlando Resort.
This family-friendly vacation home offers private pool and spa access, a game room with ping pong and air hockey, and includes baby gear, sleeping up to 15 guests with keyless entry and 24-hour security.
3 Bedroom 2 Bathroom Villas At Sevendwarfs 21-103 - Kissimmee, FL
8.0 3 reviews
Kissimmee, FL
07/21 – 07/31
$158/nighttotal: $1580 (10 )

3 Bedroom 2 Bathroom Villas At Sevendwarfs 21-103

3 4
house , Kissimmee
This Kissimmee villa is conveniently located 7.1 miles from Disney Springs, 7.2 miles from Gatorland, and 7.2 miles from ESPN Wide World of Sports.
This 1,290-square-foot vacation home boasts three bedrooms, two bathrooms, sleeps up to 11 guests, and features a private pool, fitness center, and tennis court, plus proximity to numerous family-friendly attractions.

Frequently Asked Questions about villa rentals in Kissimmee, FL

  • What are the must-see attractions in Kissimmee?

    Kissimmee is home to some of the most famous theme parks in the world, like Walt Disney World, Universal Orlando Resort, and SeaWorld Orlando. You can't visit Kissimmee without experiencing at least one of these mega-parks. Of course, there are other attractions in Kissimmee like the 'Old Town' area with its historic buildings and shops, or the 'Celebration' town center, a planned community with a charming downtown area.
  • What are the best villa rentals in Kissimmee, FL?

  • What are the top cultural attractions in Kissimmee that culture lovers should not miss?

    Culture lovers in Kissimmee should not miss attractions like the Osceola County Historical Society Pioneer Village, the Osceola Arts, and the Museum of Military History, which offer insights into the region's history and cultural heritage.
  • What indoor activities for families are available in Kissimmee on rainy days?

    On rainy days, you can head to the 'WonderWorks' amusement park, a unique upside-down building with interactive exhibits. Another great option for a rainy day is the 'Dinosaur World' museum, which has life-sized dinosaur models and fossil exhibits. If you're looking for something a little more relaxed, the 'Kissimmee Museum of History' has exhibits on the history of the area.
  • What are the best villa rentals with a pool in Kissimmee, FL?

  • Are there any nearby UNESCO sites of profound cultural or natural significance in Kissimmee?

    While there are no UNESCO sites in Kissimmee, nearby attractions like the Everglades National Park or the Castillo de San Marcos in St. Augustine hold profound cultural and natural significance.
  • What are the best activities in Kissimmee?

    Kissimmee has something for everyone, from thrill seekers to nature lovers. You can spend your days at the theme parks, exploring the 'Kissimmee Prairie Preserve State Park' with its hiking trails and wildlife, or relaxing at one of the many water parks in the area. For a unique experience, try airboating through the 'Everglades' to see alligators and other wildlife.
  • What are the best villa rentals with a jacuzzi in Kissimmee, FL?

  • Are there opportunities to learn about traditional customs or take workshops in local crafts or cooking in Kissimmee?

    Yes, visitors to Kissimmee can learn about traditional customs and take workshops in local crafts or cooking at places like the Osceola Arts or through cultural organizations like the Osceola County Historical Society.
  • What are the advantages of renting a house or a villa in Kissimmee

    Renting a house or a villa in Kissimmee can be a great option for families or groups. You'll have more space and privacy than a hotel room, and many rentals come with amenities like a private pool and a fully equipped kitchen. You can also save money on dining out by cooking meals at home.
  • What are the best villa rentals for families and kids in Kissimmee, FL?

  • Are there local guides, lecturers, or resources offering deeper insights into Kissimmee's culture?

    Kissimmee offers local guides, lecturers, and resources like the Osceola County Historical Society, the Osceola Arts, and the Osceola County Welcome Center and History Museum, which provide deeper insights into the region's culture through tours, lectures, and exhibits.
  • What exclusive experiences are available when visiting Kissimmee?

    You can have a unique experience in Kissimmee by taking a hot air balloon ride over the 'Kissimmee Prairie Preserve State Park' at sunrise. You can also go on a guided tour of the 'Walt Disney World' resort, which includes behind-the-scenes access to some of the most iconic attractions.
  • What are the best pet friendly villa rentals in Kissimmee, FL?

  • What are the best cultural activities and events in Kissimmee that one should attend?

    Attend events like the Osceola County Fair, the Kissimmee Sculpture Experience, or performances at the Osceola Arts to experience the best of Kissimmee's cultural activities and events.
  • Which part of Kissimmee would be ideal for a villa rental?

    The area around 'Celebration' is a great location for a villa rental. It's close to all of the theme parks and other attractions, but it also has a more relaxed atmosphere. The 'Reunion Resort' is another popular area for villa rentals, with its world-class amenities.
  • What are the best villa rentals with parking in Kissimmee, FL?

  • Are there any local markets or shops in Kissimmee that sell traditional local crafts and goods?

    Yes, visitors can explore local markets like the Celebration Farmers Market, the Osceola County Farmers Market, or boutique shops in downtown Kissimmee that sell traditional local crafts and goods, providing opportunities to support local artisans and find unique souvenirs.

Destinations nearby

Best Kissimmee, FL houses with parking

⁕ Disney Parks! Luxury Resort Villa • Private Pool - Kissimmee, FL
9.9 154 reviews
Kissimmee, FL
07/26 – 07/30
$265/nighttotal: $1060 (4 )

⁕ Disney Parks! Luxury Resort Villa • Private Pool

1 8
house , Kissimmee
This single-story villa is located in the Terra Verde Resort area of Kissimmee, Florida, minutes from Walt Disney World, Universal Studios, and SeaWorld.
The 4-bedroom, 2-bathroom vacation home sleeps 8 guests and boasts a private heated pool, fully equipped kitchen, dedicated workspace, and access to resort amenities including a shared pool, gym, and movie theater.
Cozy Family 4-bedroom Bella Vida Home Near Disney World - Kissimmee, FL
9.0 63 reviews
Kissimmee, FL
01/01 – 01/08
$270/nighttotal: $1890 (7 )

Cozy Family 4-bedroom Bella Vida Home Near Disney World

4 2
house , Kissimmee
This 4-bedroom, 4-bathroom vacation home is located in the Bella Vida Resort, just a 10-minute drive from Walt Disney World, with a shopping center, restaurants, and a Walmart within walking distance. The house has earned excellent ratings for location, cleanliness, and overall user experience.
This spacious 2060-square-foot home comfortably sleeps up to 12 guests. Enjoy amenities such as a private pool and spa, a fully equipped kitchen, a Minions-themed bedroom, an outdoor patio, a BBQ, and access to the resort's clubhouse.
Montego Bay 4br Villa Near Disney - Kissimmee, FL
Kissimmee, FL
07/15 – 08/27
$129/nighttotal: $5547 (43 )

Montego Bay 4br Villa Near Disney

5 4
house , Kissimmee
This 4-bedroom villa in Montego Bay, Kissimmee, offers a family-friendly retreat just 15 miles from Walt Disney World Resort and close to Universal Studios.
This Holistays property accommodates up to 8 guests with 3 bathrooms, a fully equipped kitchen, free WiFi, and on-site parking, plus access to community amenities like a pool and tennis courts.
Cozy Vacation Retreat In Fiesta Key Community - Kissimmee, FL
Kissimmee, FL
07/31 – 08/02
$233/nighttotal: $466 (2 )

Cozy Vacation Retreat In Fiesta Key Community

3 2
house , Kissimmee
This vacation home in Kissimmee's Fiesta Key Community is located approximately 10 miles from attractions including Disney's Wide World of Sports and Gatorland.
This 1460 square foot house offers 3 bedrooms, 3 bathrooms, and can accommodate up to 10 guests with amenities like a full kitchen, dishwasher, and free Wi-Fi.

Best Kissimmee, FL houses with a garden

Home Away From Home - Kissimmee, FL
8.8 4 reviews
Kissimmee, FL
08/14 – 08/16
$271/nighttotal: $542 (2 )

Home Away From Home

1 6
house , Kissimmee
This Kissimmee vacation home is conveniently located approximately 10 miles from Gatorland and Disney's Wide World of Sports, offering easy access to major theme parks.
This 280-square-foot property boasts one bedroom, three bathrooms, and accommodates up to 19 guests, featuring a private hot tub, pool, and fully equipped kitchen; plus, enjoy on-site garden access, fishing, and canoeing.
139pbd-svh Lovely New Townhome! - Kissimmee, FL
8.9 46 reviews
Kissimmee, FL
07/11 – 07/20
$265/nighttotal: $2385 (9 )

139pbd-svh Lovely New Townhome!

3 4
house , Kissimmee
This 3-bedroom vacation rental is conveniently located in Kissimmee, just 9 miles from popular attractions like Disney Springs, Disney's Boardwalk, and Disney's Hollywood Studios. Guest reviews highlight the excellent location, very good cleanliness, and very good overall experience.
The 160 square foot house offers a fully equipped kitchen, a private patio, and a washing machine. Guests can enjoy amenities like a swimming pool, a fitness center, and free Wi-Fi.
Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #52937 - Kissimmee, FL
8.6 98 reviews
Kissimmee, FL
07/13 – 07/17
$693/nighttotal: $2772 (4 )

Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #52937

10 15
house , Kissimmee
Storey Lake Resort 655 is located in Kissimmee, close to Shingle Creek Regional Park, Capone's Dinner Show, Kissimmee Go-Karts, and Lake Buena Vista Factory Stores. The resort has received very good user ratings, an excellent location rating, and a very good cleanliness rating.
This 10-bedroom vacation home spans 4,310 square feet. Enjoy a private pool, indoor and outdoor pools, a spa tub, an arcade/game room, a fully equipped kitchen, an outdoor patio, and a fitness center.
Magical 5-bedroom Villa Near Universal's Wizarding World - Kissimmee, FL
10 1 review
Kissimmee, FL
07/01 – 07/02
$557/nightfor 1 night

Magical 5-bedroom Villa Near Universal's Wizarding World

5 2
house , Kissimmee
This 5-bedroom villa in Kissimmee is located 7.6 miles from Gatorland and 10 miles from Disney Springs and Disney's Hollywood Studios.
This 2700 square foot home offers air conditioning, a private swimming pool, a garden, and a fully equipped kitchen, accommodating up to 23 guests with WiFi and parking available.
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