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2026-11-07
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Holiday Homes in Kissimmee

8815 Macapa Drive

8815 Macapa Drive, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 8-bedroom 8815 Macapa Drive Villa Kissimmee is suitable for up to 20 people and is located 2.9 km from Rum Run. Providing guests with Wi-Fi and private parking… More

From US$ 328 Book Now

392 Oc - 4Br Splendor: Private Pool

392 Ocean Course Av, Kissimmee, United States Show map

The 4-bedroom 392 Oc - 4Br Splendor: Private Pool Villa Kissimmee is situated within a 7-km distance of West Gate Flea Market and provides a Jacuzzi, ensuring a relaxing stay. Featuring lake views… More

From US$ 206 Book Now

8 Bd 5 Ba Champions Gate 1193 Cd

1193 Challenge Drive, Kissimmee, United States Show map

Located around a 10-minute ride from Highlands Reserve GC, the 8-bedroom 8 Bd 5 Ba Champions Gate 1193 Cd Villa Kissimmee has a swimming pool and is ideal for up to 22 guests. More

From US$ 541 Book Now

Luxury 6 Bedroom 5 Bath Pool Home 200

670 Sticks Street, Kissimmee, United States Show map

Featuring a heated pool, the 6-bedroom Luxury 6 Bedroom 5 Bath Pool Home 200 Kissimmee is suitable for up to 16 people and is located within 3 km of Highlands Reserve Boulevard. Providing guests with… More

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Disney Area Villa - Lake View, South-Facing Pool & Fun Game Room

1396 Seasons Blvd, Kissimmee, United States Show map

During the stay at Disney Area Villa - Lake View, South-Facing Pool & Fun Game Room Kissimmee, guests can indulge in horseback riding or visit Shingle Creek Regional Park, located 25 minutes' walk… More

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4 Bd 3 Ba Storey Lake 4817 Ll

4817 Lullaby Lane, Kissimmee, United States Show map

With a maximum capacity of 12 guests, the 1-bedroom 4 Bd 3 Ba Storey Lake 4817 Ll Kissimmee villa provides them with a heated pool and access to such wellness attractions as Give Kids The World… More

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Cozy 3 Bed 3 Bath Townhome With Fast Wifi Pools-Jacuzzi Near Disney

8133 Roseville Boulevard, Kissimmee, United States Show map

The 3-bedroom Cozy 3 Bed 3 Bath Townhome With Fast Wifi Pools-Jacuzzi Near Disney Kissimmee villa is located 3.9 km from Orlando Tree Trek Adventure Amusement Park Zip Line and provides table tennis… More

From US$ 355 Book Now

Once Upon A Stay

4908 Coral Castle Dr, Kissimmee, United States Show map

The 3-bedroom Once Upon A Stay Kissimmee villa offers swift access to various city sites, such as Eagle Pointe South, situated only 6 minutes' walk away. Providing guests with Wi-Fi and parking, the… More

From US$ 79 Book Now

3Br Home Near Disney At Emerald Island

8564 Crystal Cove Loop, Kissimmee, United States Show map

3Br Home Near Disney At Emerald Island Kissimmee with a convenient location within a 400-metre distance of Emerald Island Boulevard entices guests with a Jacuzzi. Offering a charging station for… More

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4 Bedrooms 3 Bathrooms Veranda Palms 4461 Np

4461 Nirvana Parkway, Kissimmee, United States Show map

Situated about 25 minutes' walk from Shingle Creek Regional Park, the 4-bedroom 4 Bedrooms 3 Bathrooms Veranda Palms 4461 Np Kissimmee villa is suitable for 8 guests and provides a swimming pool for… More

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1120-Spacious 4Br All Suites - 20 Min To Disney

1120 Arisha Drive, Kissimmee, United States Show map

During the stay at 1120-Spacious 4Br All Suites - 20 Min To Disney Kissimmee villa, guests can indulge in ping pong and billiard or visit Old Town Shopping Mall, located 6 km away. Located a 10… More

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Bsv2633 Luxury 7Bedroom Villa In Emerald Island

2633 Emerald Island Blvd, Kissimmee, United States Show map

Featuring a private parking lot, the 7-bedroom Bsv2633 Luxury 7Bedroom Villa In Emerald Island Kissimmee is located in the West Kissimmee district of Kissimmee and within 6 km of such cultural… More

From US$ 315 Book Now

4978 Luxurious 4Br Sunshine Getaway At Storey Lake

4978 Windermere Ave, Kissimmee, United States Show map

Featuring a swimming pool for guests' relaxation, the 4-bedroom 4978 Luxurious 4Br Sunshine Getaway At Storey Lake Kissimmee villa is located within a 3-km distance of the adventure-themed Congo… More

From US$ 215 Book Now

Cozycove Near Disney Universal Pool Home Sleeps 10

2603 Fern Cove Way, Kissimmee, United States Show map

Located approximately 6 km from Forgotten Citrus Center Monument #2, the 3-bedroom Cozycove Near Disney Universal Pool Home Sleeps 10 Kissimmee has a heated pool and is ideal for up to 10 guests. More

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3 Bd 2 Ba Lucaya Village 18-102

5362 Diplomat Court Unit 18-102, Kissimmee, United States Show map

Featuring a car park, 3 Bd 2 Ba Lucaya Village 18-102 Kissimmee villa is located in the Celebration district and 1.1 km from such cultural tourist attractions as Museum of Military History. More

From US$ 188 Book Now

Stunning Home Private Pool Great Location

Kings Castle Circle 4793, Kissimmee, United States Show map

Located nearly 25 minutes' walk from Fantasy Surf, the 6-bedroom Stunning Home Private Pool Great Location Kissimmee boasts an outdoor swimming pool with a Jacuzzi. More

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Pool Themes Game Room

1801 Sawyer Palm Place, Kissimmee, United States Show map

Situated approximately a 25-minute walk from Highlands Reserve Boulevard, the 7-bedroom Pool Themes Game Room Kissimmee villa offers guests to enjoy an aqua park and a golf course. Nestled in the… More

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Orlando Area Vacation Rental With Private Pool

2907 Banana Palm Drive, Kissimmee, United States Show map

Featuring a heated pool, the 4-bedroom Orlando Area Vacation Rental With Private Pool Kissimmee villa is suitable for up to 10 people and is located 4.4 km from Windsor Hills. Providing guests with… More

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4Br House With Game Room Near Disney

4906 Clock Tower Dr, Kissimmee, Fl 34746, Usa, Kissimmee, United States Show map

Featuring a swimming pool, the 4-bedroom 4Br House With Game Room Near Disney Kissimmee villa is suitable for up to 8 people and is located 3.4 km from Museum of Military History. More

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1716 Lima Avenue

1716 Lima Avenue, Kissimmee, United States Show map

Situated in the West Kissimmee district of Kissimmee, approximately 25 minutes' walk from Rum Run, the 6-bedroom 1716 Lima Avenue Villa Kissimmee comes with an outdoor swimming pool for guests to… More

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1696Aytownhouse 4 Beds & 4,5 Baths With Private Pool

1696 Tropical Palms Cir, Kissimmee, United States Show map

Featuring a heated pool, the 4-bedroom 1696Aytownhouse 4 Beds & 4,5 Baths With Private Pool Villa Kissimmee is suitable for up to 12 people and is located about a 25-minute walk from Rum Run. More

From US$ 188 Book Now

Near Disney Parks: Home W/ Pool In Davenport!

1000 Leader St, Kissimmee, United States Show map

Featuring a heated pool, the 4-bedroom Near Disney Parks: Home W/ Pool In Davenport! Kissimmee is suitable for up to 10 people and is located around 10 minutes' drive from Tuscan Hills Boulevard. More

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Modern Condo Near Disney Foosball Water Park

3150 Paradox Circle #306, Kissimmee, United States Show map

During the stay at the welcoming Modern Condo Near Disney Foosball Water Park Kissimmee villa, guests can indulge in mini golf or visit Old Town Shopping Mall, located 4.4 km away. Located a 10… More

From US$ 168 Book Now

4552 Bella Vida 2

4552 Alberto Cir, Kissimmee, United States Show map

Situated just 1.5 km from Shingle Creek Regional Park, the 1-bedroom 4552 Bella Vida 2 Villa Kissimmee entices guests with a Jacuzzi, ensuring a more relaxing stay. This Kissimmee villa can… More

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4 Bedrooms 3 Bathrooms Storey Lake 2617 Rt

2617 Reading Trail, Kissimmee, United States Show map

Located a 25-minute stroll from Medieval Times Dinner & Tournament, 4 Bedrooms 3 Bathrooms Storey Lake 2617 Rt Kissimmee villa has a swimming pool and is ideal for up to 8 guests. More

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Price Drop! Oct-Nov! 8Br - Theater - Game Room - Themed Rooms - Pool & Jacuzzi!

8845 Cruden Bay Court, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 8-bedroom Price Drop! Oct-Nov! 8Br - Theater - Game Room - Themed Rooms - Pool & Jacuzzi! Kissimmee villa is suitable for up to 17 people and is located about… More

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7650 Comrow #204

7650 Comrow Street, Kissimmee, United States Show map

The 3-bedroom 7650 Comrow #204 Villa Kissimmee is situated only a few steps from A World of Orchids and offers guests to relax with a Jacuzzi. The Kissimmee villa boasts a location in the Celebration… More

From US$ 284 Book Now

Upstay Mansion W Cinema Games Pool- Sleeps 24

Shanti Drive 2560, Kissimmee, United States Show map

Offering a Jacuzzi for a relaxing experience, Upstay Mansion W Cinema Games Pool- Sleeps 24 Kissimmee villa is located 10 minutes' drive from Museum of Military History. The 12-bedroom holiday home… More

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Tropical Oasis Cottage With Private Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 3021La

3021 Latitude Lane, Kissimmee, United States Show map

Located merely 6 minutes' walk from Splendid China, the 3-bedroom Tropical Oasis Cottage With Private Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 3021La Kissimmee offers… More

From US$ 494 Book Now

Sophisticated 6Br At Storey Lake Sl2766

2766 Bookmark Drive, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the welcoming Sophisticated 6Br At Storey Lake Sl2766 Kissimmee villa is located in an entertainment part of Kissimmee, 20 minutes' walk from the miniature Congo… More

From US$ 313 Book Now

5Br Private Pool Home At Veranda Palms

2613 Santosh Cove, Kissimmee, United States Show map

Offering an indoor pool for a relaxing experience, 5Br Private Pool Home At Veranda Palms Kissimmee is located a 25-minute walk from Medieval Times Dinner & Tournament. The 5-bedroom villa features… More

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Comfy Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8029Sb

8029 Sand Bar Drive, Kissimmee, United States Show map

During the stay at Comfy Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8029Sb Kissimmee, guests can indulge in a Jacuzzi or visit the film-centric theme park… More

From US$ 321 Book Now

Bright Big Home W/ Pool, Game Room & Resort Access

1690 Lima Ave, Kissimmee, United States Show map

The 8-bedroom Bright Big Home W/ Pool, Game Room & Resort Access Kissimmee is located 4.9 km from Windsor Hills and provides diving, canyoning, and billiard for active guests. The villa boasts a… More

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4Br Private Pool Home Near Disney

2002 Majorca Dr, Kissimmee, United States Show map

The 4-bedroom 4Br Private Pool Home Near Disney Kissimmee is located approximately 10 minutes' drive from Emerald Island Boulevard and provides a Jacuzzi. The accommodation boasts a patio and… More

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Home In Kissimmee

60 Cordona Drive, Kissimmee, United States Show map

Located about a 15-minute drive from Osceola Schools Environmental Study Center, the 1-bedroom Home In Kissimmee has a swimming pool and is ideal for up to 4 guests. More

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Bright Reunion Villa Near Disney

7797 Somersworth Drive, Kissimmee, United States Show map

The 4-bedroom Bright Reunion Villa Near Disney Kissimmee entices active guests with access to a fitness club and is located approximately 15 minutes' drive from Arnold Palmer Golf Course. More

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Luxury 5 Bedroom W/ Private Pool Close To Disney 8875

8875 Geneve Court, Kissimmee, United States Show map

The 5-bedroom Luxury 5 Bedroom W/ Private Pool Close To Disney 8875 Kissimmee villa entices active guests with access to a fitness centre and is located approximately a 10-minute ride from Publix… More

From US$ 419 Book Now

Le Reve 4 Bedroom Vacation Home 4404

4404 Le Reve Ct, Kissimmee, United States Show map

Offering a swimming pool, the 4-bedroom Le Reve 4 Bedroom Vacation Home 4404 Kissimmee is located about 500 metres from Give Kids The World Village Resort and is ideal for up to 10 guests. Providing… More

From US$ 369 Book Now

4Bdr With Pool Near Disney 1014

1014 Tourmaline Drive, Kissimmee, United States Show map

Staying at the 4-bedroom 4Bdr With Pool Near Disney 1014 Kissimmee villa, guests can visit lake berkley, which is only 1.3 km away. The Kissimmee holiday home is suitable for up to 8 guests and… More

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Stylish Retreat With A Private, Heated Pool, Central Ac, & Garage Game Room

4674 Cumbrian Lakes Dr, Kissimmee, United States Show map

Stylish Retreat With A Private, Heated Pool, Central Ac, & Garage Game Room Kissimmee villa is located a 5-minute walk from cumbrian lakes and invites guests to join diving, canyoning, and cycling. More

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Cozy Retreat Near Disney World & Attractions

7637 Heritage Crossing Way, Kissimmee, United States Show map

Located nearly a 20-minute walk from Watson Golf Course, the 3-bedroom Cozy Retreat Near Disney World & Attractions Kissimmee villa features an outdoor swimming pool, a hot tub, ensuring a relaxing… More

From US$ 279 Book Now

15 Bd 165 Ba Sonoma Resort 4061 Sb

4061 Sonoma Boulevard, Kissimmee, United States Show map

Hosting up to 40 guests, the 2-bedroom 15 Bd 165 Ba Sonoma Resort 4061 Sb Kissimmee villa offers a convenient location nearly 25 minutes' walk from sports attractions such as the miniature Pirates… More

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3231 Ed - The Hub Modern 3Br

3231 Energy Dr, Kissimmee, United States Show map

Situated 4.8 km from Pandora, the 2-bedroom 3231 Ed - The Hub Modern 3Br Villa Kissimmee offers guests to enjoy an aqua park and spa therapy. With a maximum capacity of 8 guests, the villa offers a… More

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Serenity At Bahama Bay For 8

605 Rum Run, Kissimmee, United States Show map

Located a mere 7 minutes' walk from Rum Run, the 3-bedroom Serenity At Bahama Bay For 8 Kissimmee villa features an outdoor swimming pool and can accommodate up to 8 guests. This property features… More

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Upstay 3Br Family-Friendly Stylish Retreat W Patio

2600 Avondale Court, Kissimmee, United States Show map

The 3-bedroom Upstay 3Br Family-Friendly Stylish Retreat W Patio Kissimmee villa accommodates up to 8 guests and offers a convenient location 3.1 km from shopping venues such as the open-air mall… More

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Upstay 15Br Villa W Games Room, Pool & Cinema

2405 Shanti Dr, Kissimmee, United States Show map

Situated nearly a 25-minute walk from the family-friendly Kissimmee Go-Karts, Upstay 15Br Villa W Games Room, Pool & Cinema Kissimmee offers guests to enjoy an aqua park, a patio, and grill. More

From US$ 1202 Book Now

5 Bd 4 Ba Paradise Palms 8869 Cp

8869 Candy Palm Road, Kissimmee, United States Show map

The 5-bedroom 5 Bd 4 Ba Paradise Palms 8869 Cp Kissimmee villa is situated only 6 minutes on foot from Paradise Palms Boulevard, featuring such comforts as Wi-Fi and a car park. Offering a convenient… More

From US$ 615 Book Now

Near Disney & Supermarket Amazing Home With Pool

Marcello Boulevard, Kissimmee, United States Show map

Featuring a swimming pool, the 4-bedroom Near Disney & Supermarket Amazing Home With Pool Kissimmee is located only 5 minutes' walk from lake berkley and is suitable for up to 13 guests. Offering a… More

From US$ 99 Book Now

Resort Home W Bbq Pool Games- Near Disney

4505 Monado Drive, Kissimmee, United States Show map

Staying at the 6-bedroom Resort Home W Bbq Pool Games- Near Disney Kissimmee, guests can easily reach the miniature Pirates Island Adventure Golf, located approximately a 20-minute walk away. With a… More

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Large Pool Home-Walk To Clubhouse-Game Room-Resort Near Disney 211

Hideaway Beach Lane 211, Kissimmee, United States Show map

Situated within a 6-km distance of Fantasy Surf, the 1-bedroom Large Pool Home-Walk To Clubhouse-Game Room-Resort Near Disney 211 Kissimmee provides fitness classes, as well as a fitness room for… More

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