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2026-11-07
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Holiday Homes in Kissimmee

Sunset Villa With Pool - Hot Tub & Theater Room!

2993 Sunset Vista Boulevard, Kissimmee, United States Show map

Located 4.3 km from the 145-foot Tree of Life Sculpture, the 5-bedroom Sunset Villa With Pool - Hot Tub & Theater Room! Kissimmee has a heated pool and is ideal for up to 11 guests. The holiday home… More

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4Br Town House With Pool 4909Nf

4909 Windermere Avenue, Kissimmee, United States Show map

During the stay at 4Br Town House With Pool 4909Nf Villa Kissimmee, guests can indulge in a Jacuzzi or visit Museum of Military History, located 3.8 km away. This 4-bedroom villa features… More

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2166Ie Townhouse 5 Bed

2166 Fleming Mist Place, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 5-bedroom 2166Ie Townhouse 5 Bed Villa Kissimmee is suitable for up to 10 people and is located 2.8 km from Rum Run. Providing guests with Wi-Fi and parking… More

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Family 4Bd Townhouse Near To Disney

4758 Terra Esmeralda Dr, Kissimmee, United States Show map

Offering access to entertainment venues such as Xtreme Paintball Xperience, situated merely 1.6 km away, the 4-bedroom Family 4Bd Townhouse Near To Disney Kissimmee villa can host up to 9 guests. More

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4 Bedrooms 3 Bathrooms Storey Lake 4925 Wa

4925 Windermere Avenue, Kissimmee, United States Show map

Featuring a heated pool, 4 Bedrooms 3 Bathrooms Storey Lake 4925 Wa Kissimmee villa is suitable for up to 8 people and is located 3.6 km from Fun Spot America Kissimmee Amusement Park. More

From US$ 1141 Book Now

Family 5Br Home With Pool At Solara

1636 Tropical Palms Cir, Kissimmee, United States Show map

Offering water slides and barbecue for guests' leisure, the 5-bedroom Family 5Br Home With Pool At Solara Kissimmee is situated approximately a 25-minute walk from Highlands Reserve Boulevard. More

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Magic Adventure In This Stunning Home In Cg

8967 Play Through Dr, Kissimmee, United States Show map

Located 3.2 km from Highlands Reserve GC, the 7-bedroom Magic Adventure In This Stunning Home In Cg Kissimmee has a swimming pool and is ideal for up to 18 guests. More

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15 Bedrooms 16 Bathrooms Sonoma 4151 Sb

4151 Sonoma Blvd, Kissimmee, United States Show map

15 Bedrooms 16 Bathrooms Sonoma 4151 Sb Kissimmee villa is located a 25-minute walk from Osceola County Welcome Center and History Museum and provides a heated pool, ensuring a relaxing stay. The 1… More

From US$ 1081 Book Now

Relaxing Lakeview 2Br Condo With 2 Clubhouses

Paradox Circle 3131, Kissimmee, United States Show map

Offering an aqua park and a patio for guests' leisure, Relaxing Lakeview 2Br Condo With 2 Clubhouses Kissimmee villa is situated a 10-minute drive from Local amusement Theme Park. Located 4.3 km from… More

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Family Getaway Near Disney - 3Br And Pool Access

5515 Paradise Cay Circle, Kissimmee, United States Show map

Accommodating up to 8 guests, the 3-bedroom Family Getaway Near Disney - 3Br And Pool Access Kissimmee villa is situated 0.7 km from renowned cultural sites such as Museum of Military History. More

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Villa Azul Townhouse

4711 Flagler Beach Way Terra Verde Resort, Kissimmee, United States Show map

Featuring an outdoor swimming pool, Villa Azul Townhouse Kissimmee is suitable for up to 8 people and is located 3 km from the nonprofit Give Kids The World Village Resort. Providing guests with Wi… More

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4Br Sedona Home W Super Mario Room Sleeps 9

4373 Desert Rose Avenue, Kissimmee, United States Show map

Situated 10 minutes by car from Makinson Island, 4Br Sedona Home W Super Mario Room Sleeps 9 Kissimmee provides access to numerous tourist attractions in the area. More

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Brand New High End 9Br Villa In Storey Lake Resort

3016 Penelope Loop, Kissimmee, United States Show map

Featuring a swimming pool, the 9-bedroom Brand New High End 9Br Villa In Storey Lake Resort Kissimmee is suitable for up to 18 people and is located within 7 km of Old Town Shopping Mall. Offering a… More

From US$ 433 Book Now

Charming And Luxury House At Champions Gate

952 Leader Street, Kissimmee, United States Show map

Featuring a swimming pool, the 4-bedroom Charming And Luxury House At Champions Gate Villa Kissimmee is suitable for up to 12 people and is located 4.6 km from Rum Run. Providing guests with Wi-Fi… More

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New Decorationresort5Brpoolfamiliescozy

3084 Juliet Dr, Kissimmee, United States Show map

Featuring a swimming pool, New Decorationresort5Brpoolfamiliescozy Kissimmee villa is suitable for up to 14 people and is located a 10-minute drive from Old Town Shopping Mall. Providing guests with… More

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Spacious 4Br Kissimmee Townhome With Modern Amenities, Perfect For Families!

5148 Crown Haven Drive, Kissimmee, United States Show map

Situated 7 km from the educational Epcot Disney Theme Park, the 2-room Spacious 4Br Kissimmee Townhome With Modern Amenities, Perfect For Families! villa entices guests to explore various tourist… More

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Modern 2Br Condo With Lazy River Near Disney

3121 Paradox Circle, Kissimmee, United States Show map

The 2-bedroom Modern 2Br Condo With Lazy River Near Disney Kissimmee villa can host up to 4 guests and is situated 4.3 km from family venues such as the creative Mortem Manor Haunted Attraction. More

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Reunion 3Br Apartment With Resort Access

7593 Gathering Drive, Kissimmee, United States Show map

Situated around a 25-minute walk from Oak Hill Baptist Church, Reunion 3Br Apartment With Resort Access Kissimmee villa provides access to numerous tourist attractions in the area. More

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Diamond - Alhambra At Poinciana 1Bd

500 Cypress Parkway, Kissimmee, United States Show map

Featuring a swimming pool, the 1-bedroom Diamond - Alhambra At Poinciana 1Bd Villa Kissimmee is suitable for up to 4 people and is located around 10 minutes by car from The Disney Wilderness Preserve… More

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Legends Palmilla Legacy

7813 Palmilla Ct, Kissimmee, United States Show map

Situated 3.9 km from Windsor Hills, the 6-bedroom Legends Palmilla Legacy Villa Kissimmee offers guests to enjoy an aqua park, a patio, and a golf course. Featuring a Jacuzzi, this holiday home is… More

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3 Bedroom 2 Bathroom Villas At Seven Dwarfs 20-104

4565 Yellowgold Road East 21-104, Kissimmee Fl, 34746, Kissimmee, United States Show map

The 3-bedroom 3 Bedroom 2 Bathroom Villas At Seven Dwarfs 20-104 Kissimmee offers proximity to such city sites as Sam's Club, located only a 5-minute walk away. The Kissimmee villa boasts an aqua… More

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Ultra-Themed Family Stay Near Disney

8447 Crystal Cove Loop, Kissimmee, United States Show map

Staying at Ultra-Themed Family Stay Near Disney Kissimmee villa, guests can visit A World of Orchids, which is approximately a 10-minute ride away. More

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Wonderful Condo To Relax And Recharge Close To Di

7661 Heritage Crossing Way, Kissimmee, United States Show map

Up to 6 guests can stay at the 3-bedroom Wonderful Condo To Relax And Recharge Close To Di Kissimmee villa and enjoy Publix Super Market at Ovation, located approximately 5 minutes' walk away. More

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Peaceful Lakeside Living: Orlando Home W/ Patio!

14918 Prairie Rose Ct, Kissimmee, United States Show map

The 3-bedroom Peaceful Lakeside Living: Orlando Home W/ Patio! Kissimmee accommodates up to 6 guests and offers a convenient location just 0.9 km from such places of worship as Catalyst Community… More

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Inviting Pool Home With Tranquil Pond View Near Theme Parks & Attractions

5506 Willow Bend Trail, Kissimmee, United States Show map

The 3-bedroom Inviting Pool Home With Tranquil Pond View Near Theme Parks & Attractions Kissimmee is located 4.6 km from Providence Golf Club and welcomes its guests to enjoy canyoning, mini golf… More

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Large 6 Bed Pool Home, Games Room, Disney 7 Miles!

2912 Banana Palm Drive, Kissimmee, United States Show map

Situated 4.2 km from Mighty Jungle Golf, Large 6 Bed Pool Home, Games Room, Disney 7 Miles! Kissimmee entices guests to explore various tourist attractions in the area. More

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5Br House Near Disney With Private Pool

2610 Santosh Cove, Kissimmee, United States Show map

Situated around 25 minutes' walk from Shingle Creek Regional Park, the 5-bedroom 5Br House Near Disney With Private Pool Kissimmee villa is suitable for 11 guests and provides a swimming pool for… More

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Private Pool, Game Room, Bbq & Free Water Park

9009 Egret Mills Terrace, Kissimmee, United States Show map

Nestled 25 minutes' walk from Highlands Reserve Boulevard, Private Pool, Game Room, Bbq & Free Water Park Kissimmee villa entices guests to explore various tourist destinations nearby. More

From US$ 251 Book Now

6 Bedrooms 5 Bathrooms Champions Gate 9223Sh

9223 Sommerset Hills Drive, Kissimmee, United States Show map

Featuring a swimming pool, the 6-bedroom 6 Bedrooms 5 Bathrooms Champions Gate 9223Sh Kissimmee villa is suitable for up to 16 people and is located 4.7 km from Rum Run. More

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3 Bedrooms 2 Bathrooms Champions Gate 8899 Cc

8899 Cabot Cliffs Drive Unit 104, Kissimmee, United States Show map

Staying at the 3-bedroom 3 Bedrooms 2 Bathrooms Champions Gate 8899 Cc Kissimmee villa, guests can visit Orlando Tree Trek Adventure Amusement Park Zip Line, which is nearly a 10-minute drive away. More

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Cap8875

8875 Candy Palm Road, Kissimmee, United States Show map

The 4-bedroom Cap8875 Villa Kissimmee is situated only 5 minutes' walk from Paradise Palms Boulevard, featuring such comforts as Wi-Fi and a car park. Offering a convenient location in the West… More

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Stunning 6 Bd House - Private Pool

8944 Cabot Cliffs Drive, Kissimmee, United States Show map

Situated within 4 km of Rum Run, the 6-bedroom Stunning 6 Bd House - Private Pool Villa Kissimmee includes a swimming pool, as well as a Jacuzzi to relax in. More

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Serene Rhyme Escape

4374 Rhyme Street, Kissimmee, United States Show map

With a maximum capacity of 10 guests, the 5-bedroom Serene Rhyme Escape Kissimmee villa provides them with a swimming pool and access to such wellness attractions as the nonprofit Give Kids The World… More

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Gorgeous Villa, Private Pool!

9041 Rhodes St, Kissimmee, United States Show map

Featuring a swimming pool, Gorgeous Villa, Private Pool! Kissimmee is suitable for up to 11 people and is located a 10-minute ride from Highgate Park Boulevard. Providing guests with Wi-Fi and a car… More

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Bella Vida Poolside Family Escape

299 Marcello Boulevard, Kissimmee, United States Show map

Located a 19-minute walk from the miniature Pirates Island Adventure Golf, Bella Vida Poolside Family Escape Villa Kissimmee has an outdoor swimming pool and is ideal for up to 16 guests. More

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Resort Condo With Pools, Hot Tub, Game Room, Tennis, Gym, Balcony, Ac, & W/D

2302 Butterfly Palm Way, Kissimmee, United States Show map

Offering a Jacuzzi for a relaxing experience, Resort Condo With Pools, Hot Tub, Game Room, Tennis, Gym, Balcony, Ac, & W/D Kissimmee villa is located a 25-minute walk from Windsor Hills. The 3… More

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645 Home At Windsor At Westside, Private Pool, And Much More!!

9054 Rhodes St, Kissimmee, United States Show map

Nestled in the West Kissimmee district of Kissimmee, the 6-bedroom 645 Home At Windsor At Westside, Private Pool, And Much More!! Kissimmee is within 5 km of Windsor Hills and offers a Jacuzzi. With… More

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Casa Com Piscina Privativa No Bella Vida Resort

4519 Monado Dr, Kissimmee, United States Show map

Featuring a swimming pool for guests' relaxation, Casa Com Piscina Privativa No Bella Vida Resort Kissimmee is located within a 7-km distance of Old Town Shopping Mall. More

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Home In West Lucaya 4Br Near Disney

8961 Shine Drive, Kissimmee, United States Show map

The 4-bedroom Home In West Lucaya 4Br Near Disney Kissimmee hosts up to 10 guests and is nestled nearly a 10-minute ride from natural sites such as Northeast Regional City Park. More

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4 Bd 3 Ba Storey Lake 4887 Rc

4887 Romeo Circle, Kissimmee, United States Show map

The 1-bedroom 4 Bd 3 Ba Storey Lake 4887 Rc Kissimmee villa is located about a 25-minute walk from the family-friendly Kissimmee Go-Karts and provides surfing for active guests. The holiday home… More

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8Br House With Game Room Near Disney Area

4477 Monado Dr, Kissimmee, United States Show map

Situated a mere 10 minutes' walk from the nonprofit Give Kids The World Village Resort, 8Br House With Game Room Near Disney Area Kissimmee villa offers guests to relax by a swimming pool. More

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6 Bedrooms 5 Bathrooms Champions Gate 601 Sb

601 Sweet Birdie Street, Kissimmee, United States Show map

Situated approximately 10 minutes' drive from Tuscan Hills Boulevard, the 6-bedroom 6 Bedrooms 5 Bathrooms Champions Gate 601 Sb Kissimmee villa provides access to numerous tourist attractions in the… More

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Florida Getaway - Spacious Home In Private Resort

741 Ocean Course Avenue, Kissimmee, United States Show map

The 2-bedroom Florida Getaway - Spacious Home In Private Resort Kissimmee entices active guests with access to a fitness studio and is located approximately a 10-minute drive from Tuscan Hills… More

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Summer In Style - 4 Bedroom Townhome With Private Pool

4976 Windermere Avenue, Kissimmee, United States Show map

Situated 3.7 km from Fun Spot America Kissimmee Amusement Park, the 4-bedroom Summer In Style - 4 Bedroom Townhome With Private Pool Kissimmee villa offers guests to enjoy an aqua park and a golf… More

From US$ 259 Book Now

Ultimate Family Vacation Home Near Disney

4954 Castle Street East, Kissimmee, United States Show map

Situated around 7 km from Indigo Lakes Golf Club, the 5-bedroom Ultimate Family Vacation Home Near Disney Kissimmee provides access to numerous tourist attractions in the area. More

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Comfortable 4Br Home With Pool At Storey Lake

4261 Paragraph Drive, Kissimmee, United States Show map

Featuring a swimming pool, Comfortable 4Br Home With Pool At Storey Lake Kissimmee is suitable for up to 10 people and is located a 10-minute drive from Museum of Military History. More

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4Br Storey Lake Resort Near Disney Private Pool

4805 Dedication Street, Kissimmee, United States Show map

Located 4 km from Old Town Shopping Mall, 4Br Storey Lake Resort Near Disney Private Pool Kissimmee villa gives access to various tourist sites in the vicinity. Featuring fitness classes, as well as… More

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Themed Bedrooms & Private Pool Gated In Fun Resort Townhouse

9045 Rhodes Street, Kissimmee, United States Show map

Situated in the West Kissimmee district of Kissimmee, approximately a 10-minute drive from Highlands Reserve Boulevard, the 4-bedroom Themed Bedrooms & Private Pool Gated In Fun Resort Townhouse… More

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Corvette Lane

2643 Corvette Lane, Kissimmee, United States Show map

The 2-bedroom Corvette Lane Kissimmee villa is located 14 minutes on foot from Old Town Shopping Mall and provides cycling, table tennis, and fisheries for active guests. Featuring a Jacuzzi, this… More

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Avenger'S, Frozen And Alice In Wonderland Themed Rooms! Private Pool And Modern Decor!

Sawyer Palm Place 1850, Kissimmee, United States Show map

Located in the West Kissimmee district, Avenger'S, Frozen And Alice In Wonderland Themed Rooms! Private Pool And Modern Decor! Kissimmee villa is a 25-minute walk from Northeast Regional City Park… More

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