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2026-11-07
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Holiday Homes in Kissimmee

Brand New Masterpiece! 15 En-Suites!

3840 Sonoma Boulevard, Kissimmee, United States Show map

Located around a 25-minute walk from the miniature Pirates Island Adventure Golf, the 15-bedroom Brand New Masterpiece! 15 En-Suites! Kissimmee villa entices guests to relax in a Jacuzzi. Guests can… More

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4Br Townhome W Private Pool Mario & Minions

4558 Baleno Lane, Kissimmee, United States Show map

Located 7 minutes' walk from Orlando Entertainment, 4Br Townhome W Private Pool Mario & Minions Kissimmee villa gives access to various tourist sites in the vicinity. More

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Stunning Retreat Townhouse 4 Beds And 10 Mins To Disney With Pool

4834 Dedication St, Kissimmee, Fl 34746, Ee. Uu., Kissimmee, United States Show map

Located 7 km from Medieval Times Dinner & Tournament, Stunning Retreat Townhouse 4 Beds And 10 Mins To Disney With Pool Kissimmee villa gives access to various tourist sites in the vicinity. The… More

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Disney Area Family Retreat With Pool And Resort Amenities

2945 Banana Palm Drive, Kissimmee, United States Show map

Staying at Disney Area Family Retreat With Pool And Resort Amenities Kissimmee villa, guests can visit Emerald Island Boulevard, which is approximately a 25-minute stroll away. More

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Luxury 6 Bedroom 5 Bath Pool Home 174

8925 Cabot Cliffs Drive, Kissimmee, United States Show map

During the stay at the 6-bedroom Luxury 6 Bedroom 5 Bath Pool Home 174 Kissimmee, guests can indulge in a Jacuzzi or visit Indian Ridge, located 4.7 km away. Located within a 10-minute drive of Rum… More

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4 Bd 3 Ba Paradise Palms 2919 Bp

2919 Banana Palm Drive, Kissimmee, United States Show map

Featuring private car parking, the 2-bedroom 4 Bd 3 Ba Paradise Palms 2919 Bp Kissimmee villa is located in the West Kissimmee district of Kissimmee and within 6 km of such cultural tourist… More

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3 Bedrooms 3 Baths Hub Westside Reserve 3257Ed

3257 Energy Drive, Kissimmee, United States Show map

Staying at the 3-bedroom 3 Bedrooms 3 Baths Hub Westside Reserve 3257Ed Kissimmee villa, guests can easily reach the 145-foot Tree of Life Sculpture, located approximately 5 km away. The Kissimmee… More

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Cozy3Brfamiliesdisneyresort Poolcozy

3229 Cupid Place, Kissimmee, United States Show map

Accommodating up to 10 guests, the 3-bedroom Cozy3Brfamiliesdisneyresort Poolcozy Kissimmee villa is situated within 6 km of renowned cultural sites such as the 145-foot Tree of Life Sculpture. More

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Disney 15 Min - Sleeps 8 - Private Pool

2643 Oneida Loop, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 4-bedroom Disney 15 Min - Sleeps 8 - Private Pool Kissimmee villa is suitable for up to 8 people and is located about 6 km from Disney's Blizzard Beach Water… More

From US$ 203 Book Now

Fiesta Siesta Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8068Dr

8068 Dreamsicle Drive, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 3-bedroom Fiesta Siesta Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8068Dr Kissimmee is located merely a 6-minute walk… More

From US$ 514 Book Now

Solara Resort 4 Bedroom Townhome- Private Pool 0929

8976 Amelia Downs Trail, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 5-bedroom Solara Resort 4 Bedroom Townhome- Private Pool 0929 Kissimmee villa is suitable for up to 8 people and is located 2.6 km from Northeast Regional City… More

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Legacy Dunes Retreat Near Disney

8921 Legacy Ct #105, Kissimmee, United States Show map

Staying at Legacy Dunes Retreat Near Disney Kissimmee villa, guests can visit the 145-foot Tree of Life Sculpture, which is approximately 6 km away. More

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Spacious Home Near Disney With Pool

2582 Shanti Drive, Kissimmee, United States Show map

The 7-bedroom Spacious Home Near Disney With Pool Kissimmee accommodates up to 16 guests and offers a convenient location 4.3 km from shopping venues such as the air mall "Lake Buena Vista Factory… More

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5Br House With Game Room Near Disney

4825 Kings Castle Cir, Kissimmee, Fl 34746, Eua, Kissimmee, United States Show map

The 5-bedroom 5Br House With Game Room Near Disney Kissimmee villa is situated just around the corner from Lennar at Storey Lake and offers guests to relax with a Jacuzzi. Featuring a swimming pool… More

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Ella Mae Getaway

Kissimmee, United States Show map

Located a 10-minute ride from Highlands Reserve GC, Ella Mae Getaway Villa Kissimmee gives access to various tourist sites in the vicinity. More

From US$ 115 Book Now

Family 3Br Townhouse Sleeps 8 Near Disney Parks 32

3204 Cupid Pl, Kissimmee, United States Show map

Featuring a car park, Gated Resort Townhouse Minutes To Disney 3204 Kissimmee villa is located in the West Kissimmee district and 6 km from such cultural tourist attractions as the 145 - foot Tree of… More

From US$ 154 Book Now

Magic At Storey Lake: 5Bd Home, 10Min From Disney

4827 Romeo Circle, Kissimmee, United States Show map

Magic At Storey Lake: 5Bd Home, 10Min From Disney Kissimmee is located a 25-minute walk from the mile-long Kissimmee Go-Karts and provides a swimming pool, ensuring a relaxing stay. More

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8999 Amelia Downs

8999 Amelia Downs Trail, Kissimmee, United States Show map

Offering a Jacuzzi for a relaxing experience, 8999 Amelia Downs Villa Kissimmee is located a 10-minute ride from Rum Run. Providing guests with Wi-Fi and a car park, the 6-bedroom holiday home is 4.9… More

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8 Bd 65 Ba Solara Resort 2326 Cs

2326 Calm Shore Way, Kissimmee, United States Show map

Situated in the West Kissimmee district of Kissimmee, around 25 minutes' walk from Highlands Reserve GC, the 3-bedroom 8 Bd 65 Ba Solara Resort 2326 Cs Kissimmee villa comes with a heated pool for… More

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Ev2709 - Enchanted Retreat Villa

2709 Bookmark Drive, Kissimmee, United States Show map

Ev2709 - Enchanted Retreat Villa Kissimmee offers easy access to such tourist spots as Lennar at Storey Lake, located only a 5-minute walk away. Providing opportunities for billiard, the Kissimmee… More

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Relaxing 4-Bedroom, 3-Bathroom Poolside Heaven In Cumbrian Lakes

4809 Cumbrian Lakes Dr., Kissimmee, United States Show map

During the stay at the 4-bedroom Relaxing 4-Bedroom, 3-Bathroom Poolside Heaven In Cumbrian Lakes Kissimmee villa, guests can indulge in canyoning, mini golf, and fisheries or visit Osceola County… More

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7407 Excitement Dr

7407 Excitement Drive, Kissimmee, United States Show map

Featuring a swimming pool, the 3-bedroom 7407 Excitement Dr Villa Kissimmee is suitable for up to 6 people and is located nearly a 15-minute ride from Corpus Christi Catholic Church. The Kissimmee… More

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8 Miles To Disney

1565 Carey Palm Circle, Kissimmee, United States Show map

Featuring a heated pool, 8 Miles To Disney Kissimmee villa is suitable for up to 10 people and is located 2 km from Rum Run. Providing guests with Wi-Fi and a car park, the 4-bedroom holiday home is… More

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Beautiful Home Close To Theme Parks With Private Pool, Ac & W/D - Dog-Friendly

4958 Castle St E, Kissimmee, United States Show map

Offering access to entertainment venues such as Kissimmee Oaks Golf Course, situated approximately 7 km away, the 5-bedroom Beautiful Home Close To Theme Parks With Private Pool, Ac & W/D - Dog… More

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Townhome Luxo 4Q C/ Piscina | Champions Gate

428 Ocean Course Avenue, Kissimmee, United States Show map

Located about 10 minutes by car from Highlands Reserve Boulevard, the 4-bedroom Townhome Luxo 4Q C/ Piscina | Champions Gate Kissimmee villa has an outdoor swimming pool and is ideal for up to 13… More

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Luxurious 4Br Home Pool Near Disney Storey Lake

4820 Memories Lane, Kissimmee, United States Show map

The 4-bedroom Luxurious 4Br Home Pool Near Disney Storey Lake Kissimmee accommodates up to 10 guests and offers a convenient location nearly 25 minutes on foot from shopping venues such as the air… More

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2781 Almaton #103

2781 Almaton Loop, Kissimmee, United States Show map

2781 Almaton #103 Villa Kissimmee is located 9 minutes' walk from Walmart and invites guests to join mini golf. Nestled in the Celebration district, the 3-bedroom holiday home features an outdoor… More

From US$ 154 Book Now

Walk To Silver Spurs Rodeo And Heritage Park Home

306 Magical Way Magic Landings, Kissimmee, United States Show map

The 4-bedroom Walk To Silver Spurs Rodeo And Heritage Park Home Kissimmee is located 4.1 km from the Grassy Kissimmee Lakefront Waterfront Park and provides a heated pool, ensuring a relaxing stay. More

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Magical 5Br Villa Game Room Pool 5Mi To Disney

2873 Simile St, Kissimmee, United States Show map

Situated around 3 km from Give Kids The World Village Resort, the 5-bedroom Magical 5Br Villa Game Room Pool 5Mi To Disney Kissimmee offers guests to enjoy spa therapy and barbecue. Featuring a hot… More

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Entire Home Near Disney Private Pool

950 Marcello Boulevard, Kissimmee, United States Show map

Entire Home Near Disney Private Pool Kissimmee provides an aqua park and a golf course for guests' leisure, and is 9 minutes' walk from the miniature Pirates Island Adventure Golf. More

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8900 Windsor Wonderland 5Bd Disney

8900 Adriatico Ln, Kissimmee, United States Show map

Located within 10 minutes' drive of Northeast Regional City Park, the 5-bedroom 8900 Windsor Wonderland 5Bd Disney Kissimmee villa has a swimming pool and is ideal for up to 11 guests. More

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Sleeps 6 Bbq Game Table Clubhouse Amenities

109 Pompano Beach Drive, Kissimmee, United States Show map

Staying at Sleeps 6 Bbq Game Table Clubhouse Amenities Villa Kissimmee, guests can easily reach Osceola County Welcome Center and History Museum, located approximately a 25-minute walk away. More

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6Br House With Private Pool Near Disney

8925 Coconut Breeze, Kissimmee, United States Show map

Located within 4 km of Emerald Island Boulevard, the 6-bedroom 6Br House With Private Pool Near Disney Kissimmee villa has a swimming pool and is ideal for up to 18 guests. Located in the West… More

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Luxury 6Br Disney Villa | Pool, Spa, Game Room, Sleeps 16+1859Sn

2649 Calistoga Avenue, Kissimmee, United States Show map

During the stay at Luxury 6Br Disney Villa | Pool, Spa, Game Room, Sleeps 16+1859Sn Kissimmee, guests can indulge in billiard or visit the mile-long Kissimmee Go-Karts, located 3.2 km away. The 6… More

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Windsor Palms Resort Vacation Home Wp2209

2209 Wyndham Palms Way, Kissimmee, United States Show map

Staying at the 4-bedroom Windsor Palms Resort Vacation Home Wp2209 Kissimmee, guests can visit Orlando Tree Trek Adventure Amusement Park Zip Line, which is nearly a 25-minute walk away. Offering… More

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Centre Court Amore

1366 Centre Court Ridge #103, Kissimmee, United States Show map

Staying at the 3-bedroom Centre Court Amore Kissimmee villa, guests can visit Reunion Resort the palmer course, which is nearly a 25-minute walk away. Featuring a Jacuzzi, this Kissimmee holiday home… More

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6 Bedrooms 5 Bathrooms Storey Lake 4763Kc

4763 Kings Castle Circle, Kissimmee, United States Show map

Situated 4 km from Local amusement Theme Park, the 6-bedroom 6 Bedrooms 5 Bathrooms Storey Lake 4763Kc Kissimmee villa is suitable for 13 guests and provides a heated pool for additional relaxation. More

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12Br Getaway Pool Theater

4473 Monado Drive, Kissimmee, United States Show map

12Br Getaway Pool Theater Villa Kissimmee is situated merely 8 minutes' walk from the nonprofit Give Kids The World Village Resort and provides a hot tub for a relaxing stay. More

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Modern Oasis 9 Bd 5 Ba Storey Lake - 2742 Ow

2742 Oxymoron Way, Kissimmee, United States Show map

Featuring a heated pool, the 9-bedroom Modern Oasis 9 Bd 5 Ba Storey Lake - 2742 Ow Kissimmee villa is suitable for up to 24 people and is located 3.8 km from Museum of Military History. More

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4169 Paragraph

4169 Paragraph Drive, Kissimmee, United States Show map

Located about a 25-minute walk from Capone's Dinner and Show, 4169 Paragraph Kissimmee villa has an outdoor swimming pool and is ideal for up to 14 guests. Guests can enjoy bowling and mini golf at… More

From US$ 571 Book Now

4Br Town House With Pool 4809Am

4809 Memories Lane, Kissimmee, United States Show map

The 4-bedroom 4Br Town House With Pool 4809Am Villa Kissimmee is located within a 4-km distance of Old Town Shopping Mall and provides cycling and fisheries for active guests. This Kissimmee holiday… More

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4Br Themed Home W Resort Pool Near Disney

5370 Diplomat Court #104, Kissimmee, United States Show map

The 4-bedroom 4Br Themed Home W Resort Pool Near Disney Kissimmee can host up to 12 guests and is situated 2.9 km from family venues such as Old Town Shopping Mall. Located around 10 minutes by car… More

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Kcc4741

4741 Kings Castle Circle, Kissimmee, United States Show map

Featuring a swimming pool, the 6-bedroom Kcc4741 Villa Kissimmee is suitable for up to 12 people and is located nearly 25 minutes' walk from the family-friendly Kissimmee Go-Karts. The property… More

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Kis105-2601-4-Pg - Shingle Creek Poolside Retreat

2601 Shingle Creek, Kissimmee, United States Show map

Ensuring a relaxing stay with a sauna, the 4-bedroom Kis105-2601-4-Pg - Shingle Creek Poolside Retreat Villa Kissimmee is situated within a 3-km distance of the Grassy Kissimmee Lakefront Waterfront… More

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Vhc493 - Sonoma Resort - 15 Bed 15 Baths Villa

2609 Yountville Avenue, Kissimmee, Fl 34741, United States, Kissimmee, United States Show map

Nestled 4 km from Eagle Park Orlando, Vhc493 - Sonoma Resort - 15 Bed 15 Baths Villa Kissimmee entices guests to explore various tourist destinations nearby. More

From US$ 1444 Book Now

5Br Themed Family Villa Near Disney With Private Pool

1531 Fairview Circle, Kissimmee, United States Show map

Situated within 25 minutes' walk of Reunion Resort the palmer course, the 1-bedroom 5Br Themed Family Villa Near Disney With Private Pool Kissimmee provides fitness classes, as well as a fitness room… More

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Casa 9Q C/ Piscina E Game Room — Perto Da Disney

7696 Fairfax Drive, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 9-bedroom Casa 9Q C/ Piscina E Game Room — Perto Da Disney Kissimmee is suitable for up to 20 people and is located 3.4 km from Windsor Hills. Providing guests… More

From US$ 908 Book Now

Ccl8538

8538 Crystal Cove Loop, Kissimmee, United States Show map

Featuring parking, the 2-bedroom Ccl8538 Villa Kissimmee is located in the West Kissimmee district and 3.9 km from such cultural tourist attractions as the 145-foot Tree of Life Sculpture. More

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Ev3009 - Grand View Retreat

3009 Protagonist, Kissimmee, United States Show map

Ev3009 - Grand View Retreat Villa Kissimmee is located within 7 km of Disney's Typhoon Lagoon Water Park and allows guests to enjoy billiard. Offering a heated pool, this Kissimmee holiday home… More

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Upstay Ultimate Orlando Retreat W Pool & Hot Tub Sleeps 16

4489 Monado Drive, Kissimmee, United States Show map

Upstay Ultimate Orlando Retreat W Pool & Hot Tub Sleeps 16 Kissimmee villa offers proximity to nearby tourist spots, such as Xtreme Paintball Xperience, situated approximately 10 minutes away by car. More

From US$ 493 Book Now