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2026-11-07
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Holiday Homes in Kissimmee

Comfort Home With Bbq, Private Pool & Hot Tub

106 Madiera Beach Boulevard, Kissimmee, United States Show map

The 5-bedroom Comfort Home With Bbq, Private Pool & Hot Tub Kissimmee is nestled within 25 minutes' walk of Shingle Creek Regional Park and provides a Jacuzzi. More

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Jamaican Breeze Villa

643 Mckinley Court, Kissimmee, United States Show map

Staying at Jamaican Breeze Villa Kissimmee, guests can easily reach The New Jerusalem Church, located nearly 10 minutes' drive away. More

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Mario Bros Game Room 8Bd Pool Movie Room 2622

2622 Calistoga Ave, Kissimmee, United States Show map

With a maximum capacity of 16 guests, the 8-bedroom Mario Bros Game Room 8Bd Pool Movie Room 2622 Kissimmee villa provides them with a swimming pool and access to such wellness attractions as the… More

From US$ 348 Book Now

Windsor Palms 4 Bedroom Vacation Home 2252

2252 Wyndham Palms Way, Kissimmee, United States Show map

Nestled nearly a 25-minute walk from A World of Orchids, the 4-bedroom Windsor Palms 4 Bedroom Vacation Home 2252 Kissimmee entices guests to explore various tourist destinations nearby. The holiday… More

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Spacious Home In Fantasyworld

3093 Rosie Ogrady Court, Kissimmee, United States Show map

The 2-bedroom Spacious Home In Fantasyworld Kissimmee is located just 6 minutes' walk from Dare 2 Escape, giving access to various tourist spots nearby. With a maximum capacity of 4 guests, the… More

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Fabulous 5Bd Single Family At Champions Gate Resort 8988

Cabot Cliffs Drive, Kissimmee, United States Show map

During the stay at the 5-bedroom Fabulous 5Bd Single Family At Champions Gate Resort 8988 Kissimmee villa, guests can indulge in cycling and fisheries or visit Northeast Regional City Park, located 4… More

From US$ 290 Book Now

6Q/5.5B Luxo Piscina Priv. Disney

2751 Lido Key Drive, Kissimmee, United States Show map

Nestled in the West Kissimmee district, the 6-bedroom 6Q/5.5B Luxo Piscina Priv. Disney Kissimmee villa is merely 13 minutes' walk from Emerald Island Boulevard and offers a Jacuzzi. This… More

From US$ 421 Book Now

Luxury Pool Home Near Disney Resort Access

2656 Reading Trail, Kissimmee, United States Show map

Offering a hot tub and an indoor pool for a relaxing experience, Luxury Pool Home Near Disney Resort Access Kissimmee is located a 25-minute walk from Medieval Times Dinner & Tournament. The 3… More

From US$ 342 Book Now

4 Mi To Disney: Family Getaway W/ Game Room!

8082 Roaring Creek Ct, Kissimmee, United States Show map

Situated 4.6 km from the 145-foot Tree of Life Sculpture, the welcoming 4 Mi To Disney: Family Getaway W/ Game Room! Kissimmee villa offers guests to enjoy a terrace and playground. Nestled in the… More

From US$ 196 Book Now

Water View Pool Home Near Disney

4759 Cumbrian Lakes Drive, Kissimmee, United States Show map

The 5-bedroom Water View Pool Home Near Disney Kissimmee hosts up to 10 guests and is nestled 3.5 km from natural sites such as Shingle Creek Regional Park. Located approximately 10 minutes' drive… More

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Beautiful 4 Bedroom 3 Bath Pool Townhome 280

4287 Paragraph Dr, Kissimmee, United States Show map

The 4-bedroom Beautiful 4 Bedroom 3 Bath Pool Townhome 280 Kissimmee villa can host up to 12 guests and is situated about a 15-minute drive from family venues such as Old Town Shopping Mall. More

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3 Bedrooms 3 Baths The Hub At Westside 3361Tt

3361 Tranquil Trail, Kissimmee, United States Show map

The 3-bedroom 3 Bedrooms 3 Baths The Hub At Westside 3361Tt Kissimmee villa offers proximity to nearby tourist spots, such as the 145-foot Tree of Life Sculpture, situated about 6 km away. Offering a… More

From US$ 244 Book Now

< 5 Mi To Disney Parks: Spacious Home W/ Lanai

2779 Picadilly Cir, Kissimmee, United States Show map

Located about 10 minutes' drive from Emerald Island Boulevard, the 4-bedroom 5 Mi To Disney Parks: Spacious Home W/ Lanai Kissimmee has a heated pool and is ideal for up to 8 guests. Offering a car… More

From US$ 239 Book Now

Paradise Palms Resort | Private Pool | Dog Friendly | 4Br Near Disney

8952 California Palm Road,, Kissimmee, United States Show map

Offering location around 15 minutes' drive from Avatar Flight of Passage Tourist Information Center, 1.5 km from Lake Davenport, the 4-bedroom Paradise Palms Resort | Private Pool | Dog Friendly |… More

From US$ 151 Book Now

Super Giant - 12Bd 12Bas - Sleep 38 & Near Disney

2551 Shanti Drive, Kissimmee, United States Show map

Situated 2.8 km from Shingle Creek Regional Park, the 12-bedroom Super Giant - 12Bd 12Bas - Sleep 38 & Near Disney Kissimmee villa is suitable for 16 guests and provides a swimming pool for… More

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Fantastic 5Br Themed Pool Home Near Disney World

1165 Seasons Boulevard, Kissimmee, United States Show map

Staying at the 5-bedroom Fantastic 5Br Themed Pool Home Near Disney World Kissimmee, guests can visit Kissimmee Oaks Golf Course, which is around 7 km away. With a maximum capacity of 10 guests, this… More

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2 Mi To Animal Kingdom: Kissimmee Resort Condo!

9061 Treasure Trove Ln Unit 201, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the welcoming 2 Mi To Animal Kingdom: Kissimmee Resort Condo! villa is suitable for up to 7 people and is located 4.2 km from Rum Run. Providing guests with Wi-Fi… More

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9Br House With Game Room Near Disney

2944 Penelope Loop, Kissimmee, Fl 34746, Eua, Kissimmee, United States Show map

Featuring a swimming pool, the 9-bedroom 9Br House With Game Room Near Disney Kissimmee villa is suitable for up to 24 people and is located approximately 25 minutes' walk from the family-friendly… More

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Superb Thematic 2Br With Waterpark & Garage

Cabot Cliffs Drive 8883, Kissimmee, United States Show map

Featuring a swimming pool, the 2-bedroom Superb Thematic 2Br With Waterpark & Garage Villa Kissimmee is suitable for up to 6 people and is located 4.7 km from Indian Ridge. More

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Mickeys Paradise - A Fabulous 4 Bed Paradise Palms Resort Pool Home That'S Close To Disney

8960 Cuban Palm Road, Kissimmee, United States Show map

Offering a sundeck and a golf course for an enjoyable stay, Mickeys Paradise - A Fabulous 4 Bed Paradise Palms Resort Pool Home That'S Close To Disney Kissimmee is merely a 5-minute walk from… More

From US$ 425 Book Now

7774 Basnett Circle

7774 Basnett Circle, Kissimmee, United States Show map

7774 Basnett Circle Villa Kissimmee is situated a mere 5 minutes' walk from Windsor Hills and provides a Jacuzzi for additional comfort. This 5-bedroom villa features opportunities for bowling and… More

From US$ 260 Book Now

2770Ag Villa 5 Beds & 5 Baths With Private Pool-Spa

2770 Bookmark Dr, Kissimmee, United States Show map

Featuring a heated pool, 2770Ag Villa 5 Beds & 5 Baths With Private Pool-Spa Kissimmee is suitable for up to 15 people and is located 2.7 km from Medieval Times Dinner & Tournament. Providing guests… More

From US$ 250 Book Now

Palm & Pine Retreat At Bahama Bay

1105 New Providence Promenade, Kissimmee, United States Show map

Offering garden views, Palm & Pine Retreat At Bahama Bay Villa Kissimmee is situated 8 minutes' walk from Rum Run. Providing guests with Wi-Fi and a charging station for electric vehicles, the 3… More

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Charming Dog-Friendly Home With Pool, Hot Tub, Fitness Center, Patio, & Kitchen

8119 Roseville Blvd, Kissimmee, United States Show map

The 3-bedroom Charming Dog-Friendly Home With Pool, Hot Tub, Fitness Center, Patio, & Kitchen Kissimmee is located approximately 10 minutes' drive from Indian Ridge and provides a Jacuzzi. The… More

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Dunmore Disney Home

4931 Dunmore Lane, Kissimmee, United States Show map

Staying at the 4-bedroom Dunmore Disney Home Kissimmee, guests can visit the mile-long Kissimmee Go-Karts, which is merely 1.9 km away. This Kissimmee holiday home is suitable for up to 12 guests and… More

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Great Community, Amazing Private Pool, Near Disney!

145 Rochester Loop, Kissimmee, United States Show map

Staying at the 5-bedroom Great Community, Amazing Private Pool, Near Disney! Kissimmee villa, guests can easily reach Rum Run, located nearly a 20-minute walk away. This Kissimmee holiday home… More

From US$ 230 Book Now

670Rg Townhouse 4 Beds & 3 Baths With Private Pool

670 Pebble Beach Dr, Kissimmee, United States Show map

Situated about 10 minutes' drive from Rum Run, the 4-bedroom 670Rg Townhouse 4 Beds & 3 Baths With Private Pool Villa Kissimmee offers guests to enjoy an aqua park and a golf course. Providing guests… More

From US$ 179 Book Now

Themed 4Br Home-Mickey & Star Wars Pool Spacious

Love Storey Lane 4814, Kissimmee, United States Show map

The 4-bedroom Themed 4Br Home-Mickey & Star Wars Pool Spacious Kissimmee entices active guests with access to a fitness suite and is located about a 15-minute drive from Fun 'n Wheels Family Fun… More

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1508 Nassau Point

1508 Nassau Point Trail, Kissimmee, United States Show map

The 5-bedroom 1508 Nassau Point Villa Kissimmee is located around 25 minutes' walk from Highlands Reserve Boulevard and provides a Jacuzzi. This property features opportunities for mini golf in the… More

From US$ 486 Book Now

7652 Otterspool

7652 Otterspool Street, Kissimmee, United States Show map

Located approximately 5 minutes' walk from A World of Orchids, the 3-bedroom 7652 Otterspool Villa Kissimmee gives easy access to various tourist attractions in the area. The property is suitable for… More

From US$ 178 Book Now

Family Reunion 10Br Villa Pool/Spa Near Disney!

4513 Target Blvd, Kissimmee, United States Show map

Situated within 25 minutes' walk of the miniature Congo River Golf, the 10-bedroom Family Reunion 10Br Villa Pool/Spa Near Disney! Kissimmee includes a swimming pool, as well as a hot tub to relax in. More

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Crystal 3 Bedroom 10 Minutes To Disney

8549 Crystal Cove Loop, Kissimmee, United States Show map

Situated approximately 25 minutes' walk from Mystic Dunes Golf Club at Mystic Dunes Resort, the 3-bedroom Crystal 3 Bedroom 10 Minutes To Disney Kissimmee villa entices guests to explore various… More

From US$ 73 Book Now

Luxury 4 Bedroom 3 Bath Pool Home 153

254 Ocean Course Av, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 4-bedroom Luxury 4 Bedroom 3 Bath Pool Home 153 Kissimmee is suitable for up to 12 people and is located 4.8 km from Highgate Park Boulevard. Providing guests… More

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4 Bd 4 Ba Bella Vida 440 Lf

440 Las Fuentes Drive, Kissimmee, United States Show map

Featuring a swimming pool, the 4-bedroom 4 Bd 4 Ba Bella Vida 440 Lf Villa Kissimmee is suitable for up to 10 people and is located 1.3 km from Medieval Times Dinner & Tournament. More

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Standard Villas Resort At Seven Dwrafs - Close To Disney

2618 Lodi Circle 104, 02, Kissimmee, United States Show map

Located just a 5-minute walk from Sam's Club, the 5-room Standard Villas Resort At Seven Dwrafs - Close To Disney Kissimmee provides guests with a Jacuzzi. This 3-bedroom villa features opportunities… More

From US$ 87 Book Now

4693Gb - Heroes & Wizards Villa

4693 Golden Beach Court, Kissimmee, United States Show map

Located approximately 25 minutes' walk from Shingle Creek Regional Park, 4693Gb - Heroes & Wizards Villa Kissimmee boasts a swimming pool with a Jacuzzi and a sauna. More

From US$ 573 Book Now

Luxury Decor 6Br At Storey Lake Sleeps 16 Sl2945

2945 Fable St, Kissimmee, United States Show map

During the stay at the welcoming Luxury Decor 6Br At Storey Lake Sleeps 16 Sl2945 Kissimmee villa, guests can indulge in a Jacuzzi or visit the adventure-themed Congo River Golf, located 3.2 km away.… More

From US$ 621 Book Now

3071 Beach Palm

3071 Beach Palm Ave, Kissimmee, United States Show map

Situated in the West Kissimmee district of Kissimmee, merely 0.7 km from Paradise Palms Boulevard, the 5-bedroom 3071 Beach Palm Kissimmee villa comes with an outdoor swimming pool for guests to… More

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Luxury 7 Bedroom 5 Bath Pool Home 209

791 Sticks Street, Kissimmee, United States Show map

Located nearly a 10-minute drive from Highlands Reserve Boulevard, Luxury 7 Bedroom 5 Bath Pool Home 209 Kissimmee has a heated pool and is ideal for up to 17 guests. The Kissimmee holiday home… More

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3Q/2B Vista Para O Lago C/Piscina | 10Min->Disney

3133 Bear Path, Kissimmee, United States Show map

Featuring a year-round outdoor swimming pool, the 3-bedroom 3Q/2B Vista Para O Lago C/Piscina | 10Min-Disney Kissimmee villa is suitable for up to 6 people and is located around 7 km from the… More

From US$ 202 Book Now

Elegant Retreat With Private Pool & Spa

333 Ocean Course Ave, Kissimmee, United States Show map

Featuring a swimming pool, the 9-bedroom Elegant Retreat With Private Pool & Spa Kissimmee villa is suitable for up to 26 people and is located about 4 km from Tuscan Hills Boulevard. Providing… More

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Elegant 5Br Home W Private Pool Emerald

2682 Emerald Island Blvd, Kissimmee, United States Show map

Situated in the West Kissimmee district of Kissimmee, within 10 minutes' drive of Pandora, the 5-bedroom Elegant 5Br Home W Private Pool Emerald Kissimmee comes with a heated pool for guests to… More

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Super Boho - Lake Toho Timeless Charm

308 Lakeshore Boulevard, Kissimmee, United States Show map

Super Boho - Lake Toho Timeless Charm Kissimmee villa, located 6 minutes' walk from Kissimmee Farmers Market, can host up to 4 guests. Located 3.4 km from Kissimmee Golf Club, the 2-bedroom holiday… More

From US$ 138 Book Now

6 Bedrooms

9123 Sommerset Hills Dr, Kissimmee, United States Show map

The 6-bedroom 6 Bedrooms Kissimmee villa, located only 6 minutes' stroll from ChampionsGate Country Club Golf, entices guests with an outdoor swimming pool as well as a Jacuzzi to relax in. The… More

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Stunning Game Room & Pool Jacuzzi Storey Lake 2799

2799 Bookmark Drive, Kissimmee, United States Show map

The 6-bedroom Stunning Game Room & Pool Jacuzzi Storey Lake 2799 Kissimmee villa entices active guests with access to a fitness suite and is located nearly a 10-minute ride from Fun 'n Wheels Family… More

From US$ 503 Book Now

Luxury 5Br Storey Lake Retreat Near Disney 2969

2969 Penelope Loop, Kissimmee, United States Show map

Situated about 10 minutes by car from Shingle Creek Regional Park, the 5-bedroom Luxury 5Br Storey Lake Retreat Near Disney 2969 Kissimmee villa is suitable for 13 guests and provides a heated pool… More

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5Br Luxury Townhome W Pool At Storey Lake Disney

2581 Reading Trail, Kissimmee, United States Show map

5Br Luxury Townhome W Pool At Storey Lake Disney Kissimmee villa is located a 25-minute walk from Fun 'n Wheels Family Fun Parks and provides a swimming pool, ensuring a relaxing stay. The 5-bedroom… More

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7718 Teascone

7718 Teascone Blvd, Kissimmee, United States Show map

Located only a 5-minute stroll from Windsor Hills, the 6-bedroom 7718 Teascone Villa Kissimmee can accommodate up to 12 guests, providing them with a Jacuzzi for a relaxing stay. The Kissimmee… More

From US$ 294 Book Now

4 Bedrooms 4 Bathrooms Solara 1568 Cp

1568 Carey Palm Circle, Kissimmee, United States Show map

Staying at the 4-bedroom 4 Bedrooms 4 Bathrooms Solara 1568 Cp Kissimmee villa, guests can easily reach Highlands Reserve GC, located nearly a 25-minute walk away. With a maximum capacity of 12… More

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4Br Retreat Pool Close To Disney

4508 Monado Dr, Kissimmee, United States Show map

Situated around 700 metres from Give Kids The World Village Resort, the 4-bedroom 4Br Retreat Pool Close To Disney Kissimmee villa is suitable for 9 guests and provides a swimming pool to relax in. More

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