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2026-11-07
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Holiday Homes in Kissimmee

Lux 4Brvilla Hot Tub Grill Private Heated Pool

4954 Bond Street East, Kissimmee, United States Show map

The 4-bedroom Lux 4Brvilla Hot Tub Grill Private Heated Pool Kissimmee villa entices active guests with access to a fitness area and is located about a 10-minute drive from The Green Barn on the Lake. More

From US$ 465 Book Now

Modern Resort House | Pool • Wi-Fi • Minutes To Disney

2657 Petition Ln Kissimmee Fl, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 5-bedroom Modern Resort House | Pool • Wi-Fi • Minutes To Disney Kissimmee villa is suitable for up to 12 people and is located 2.6 km from Oren Brown… More

From US$ 644 Book Now

5Br Family Fun Home - Game Room & Private Pool

153 Barefoot Beach Way, Kissimmee, United States Show map

Situated within 6 km of Kissimmee Oaks Golf Course, the 5-bedroom 5Br Family Fun Home - Game Room & Private Pool Kissimmee includes an outdoor swimming pool, as well as a hot tub to relax in. More

From US$ 443 Book Now

5Br 5Bath Pvt Home Bbq Pool 10Min Disney 3077Ft

4773 Kings Castle Circle,, Kissimmee, United States Show map

The 5-bedroom 5Br 5Bath Pvt Home Bbq Pool 10Min Disney 3077Ft Kissimmee entices active guests with access to a fitness area and is located nearly a 10-minute ride from Fantasy Surf. Offering an… More

From US$ 481 Book Now

New To Market 5 Bed - Storey Lake Retreat

Reading Trail 2501, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 5-bedroom New To Market 5 Bed - Storey Lake Retreat Kissimmee villa is suitable for up to 10 people and is located 3.9 km from Museum of Military History. More

From US$ 229 Book Now

Family Getaway Townhome At Lake Berkley 15Min To Disney

967 Park Terrace Cir, Kissimmee, United States Show map

Located just moments from lake berkley, the 2-room Family Getaway Townhome At Lake Berkley 15Min To Disney Kissimmee villa gives easy access to various tourist attractions in the area. Staying at the… More

From US$ 145 Book Now

Beautiful Hollywood Style Home Next To Disney

3081 Seaview Castle Drive, Kissimmee, United States Show map

Beautiful Hollywood Style Home Next To Disney Kissimmee enjoys a convenient location, within 900 metres of Dare 2 Escape, and offers guests to unwind in a solarium. Guests can enjoy mini golf at the… More

From US$ 148 Book Now

Gorgeous 4 Bedroom W Screened Pool Close To Disney 2653

Reading Trail 2653, Kissimmee, United States Show map

The 4-bedroom Gorgeous 4 Bedroom W Screened Pool Close To Disney 2653 Kissimmee villa is located around 25 minutes' walk from Osceola County Welcome Center and History Museum and allows guests to… More

From US$ 205 Book Now

Family Friendly Four Bedrooms 5145

5145 Adelaide Drive, Kissimmee, United States Show map

The 4-bedroom Family Friendly Four Bedrooms 5145 Kissimmee villa can host up to 10 guests, boasting a convenient location nearly 25 minutes' walk from iconic cultural attractions such as Museum of… More

From US$ 138 Book Now

1061 Lake Berkley 4 Bed With Pool&Spa

1061 Lake Berkley Drive, Kissimmee, United States Show map

The 4-bedroom 1061 Lake Berkley 4 Bed With Pool&Spa Kissimmee villa enjoys a serene location a mere 1.4 km from wellness venues like the themed Give Kids The World Village Resort and provides guests… More

From US$ 146 Book Now

Gorgeous 4Bd Close To Disney With Pool At Storey Lake 4403

Scene Lane 4403, Kissimmee, United States Show map

Offering a location 3.1 km from Dare 2 Escape, Gorgeous 4Bd Close To Disney With Pool At Storey Lake 4403 Kissimmee villa gives access to various tourist spots in the area. More

From US$ 575 Book Now

Kissimmee Sunshine

8542 Bay Lilly Loop, Kissimmee, United States Show map

Staying at Kissimmee Sunshine Villa, guests can visit Disney's Blizzard Beach Water Park, which is nearly a 15-minute ride away. More

From US$ 231 Book Now

Upstay Luxury Resort Mansion W Pool Near Disney

Calistoga Avenue 2610, Kissimmee, United States Show map

Nestled a 25-minute walk from Plaza del Sol Mall, Upstay Luxury Resort Mansion W Pool Near Disney Kissimmee villa entices guests to explore various tourist destinations nearby. More

From US$ 246 Book Now

Private Pool At Hidden Gem Ready For Your Family:)

103 Pansy Court, Kissimmee, United States Show map

Offering a location 2.9 km from Catalyst Community Christian Church, Private Pool At Hidden Gem Ready For Your Family:) Kissimmee villa gives access to various tourist spots in the area. More

From US$ 98 Book Now

Cozy Kissimmee Townhome About 8 Mi To Disney World!

1089 Park Ridge Cir, Kissimmee, United States Show map

Nestled a 17-minute walk from Medieval Times Dinner & Tournament, Cozy Kissimmee Townhome About 8 Mi To Disney World! villa entices guests to explore various tourist destinations nearby. More

From US$ 98 Book Now

Family Friendly Four Bedrooms W/ Pool 4896

4896 Windermere Avenue, Kissimmee, United States Show map

Accommodating up to 12 guests, the 4-bedroom Family Friendly Four Bedrooms W/ Pool 4896 Kissimmee villa is situated around 10 minutes by car from renowned cultural sites such as Museum of Military… More

From US$ 176 Book Now

Marvelous 2 Bd Apt Close To Disney At Storey Lake 106

Paradox Circle, Kissimmee, United States Show map

The 2-bedroom Marvelous 2 Bd Apt Close To Disney At Storey Lake 106 Kissimmee villa is located around 25 minutes' walk from the family-friendly Kissimmee Go-Karts and provides cycling, ping-pong, and… More

From US$ 197 Book Now

Beautiful Furnished Townhome W Private Pool

1616 Carey Palm Circle, Kissimmee, United States Show map

Situated nearly a 25-minute walk from Highlands Reserve Boulevard, the 1-bedroom Beautiful Furnished Townhome W Private Pool Kissimmee villa offers guests to enjoy water slides, a patio, and… More

From US$ 584 Book Now

Marvelous 4Bd With Pool At Storey Lake Resort 2601

Reading Trail 2601, Kissimmee, United States Show map

Situated nearly 25 minutes on foot from the miniature Pirates Island Adventure Golf, the 4-bedroom Marvelous 4Bd With Pool At Storey Lake Resort 2601 Kissimmee villa offers crib and a changing table… More

From US$ 202 Book Now

Luxury Home With Pool & 6 Beds Near Disney

3127 Fairfield Drive, Kissimmee, United States Show map

Located nearly a 15-minute drive from Silver Spur Rodeo Arena, the 3-bedroom Luxury Home With Pool & 6 Beds Near Disney Kissimmee has an outdoor swimming pool and is ideal for up to 9 guests. More

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Four Bedrooms At Compass Bay Resort

5162 Adelaide Drive, Kissimmee, United States Show map

Offering an aqua park, spa therapy, and a patio for guests' leisure, Four Bedrooms At Compass Bay Resort Kissimmee villa is situated about 7 km from the educational Epcot Disney Theme Park. The 4… More

From US$ 175 Book Now

Perfect Vacation Gated Resort With Private Pool

4760 Vero Beach Place, Kissimmee, United States Show map

With the capacity to host 8 guests, the 4-bedroom Perfect Vacation Gated Resort With Private Pool Kissimmee villa is located approximately 25 minutes' walk from such significant cultural landmarks as… More

From US$ 139 Book Now

This Happy Place

8931 Bismarck Palm Road, Kissimmee, United States Show map

The 4-bedroom This Happy Place Kissimmee villa boasts a location within 5 minutes' walk of Paradise Palms Boulevard and offers guests to enjoy live performances. Located within 7 km of the 145-foot… More

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Super Nice And Spacious 9Bdr Home

Sommerset Hills Drive 9202, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the welcoming Super Nice And Spacious 9Bdr Home Kissimmee is located in an entertainment part of Kissimmee, a 10-minute ride from Rum Run. Providing guests with Wi… More

From US$ 314 Book Now

4Br House W Perfect Location Pool And Much More

8156 Fan Palm Way, Kissimmee, United States Show map

Hosting up to 9 guests, the 4-bedroom 4Br House W Perfect Location Pool And Much More Kissimmee villa offers a prime location within a 6-km distance of sports attractions such as the 220-acre multi… More

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2696 Manesty

2696 Manesty Lane, Kissimmee, United States Show map

Situated only 5 minutes on foot from Windsor Hills, the 6-bedroom 2696 Manesty Villa Kissimmee can host up to 12 guests and offers a Jacuzzi, ensuring a relaxing stay. Featuring a games room to make… More

From US$ 354 Book Now

Four Bedrooms Close To Disney W Pool 4898

4898 Windermere Avenue, Kissimmee, United States Show map

The 4-bedroom Four Bedrooms Close To Disney W Pool 4898 Kissimmee villa can host up to 13 guests, boasting a convenient location around a 10-minute drive from iconic cultural attractions such as… More

From US$ 193 Book Now

2947 Paradise Palms 5Br Townhome With Pool & Themed Rooms

2947 Banana Palm Drive, Kissimmee, United States Show map

Featuring a swimming pool, the 5-bedroom 2947 Paradise Palms 5Br Townhome With Pool & Themed Rooms Kissimmee villa is suitable for up to 10 people and is located about 6 km from the 145 - foot Tree… More

From US$ 217 Book Now

4 Bedroom Hot Tub Cozy Decor @ Regal Oaks Ro2761N

2761 Corvette Ln, Kissimmee, United States Show map

The 4-bedroom 4 Bedroom Hot Tub Cozy Decor @ Regal Oaks Ro2761N Kissimmee villa can host up to 8 guests, boasting a convenient location within 25 minutes' walk of iconic cultural attractions such as… More

From US$ 249 Book Now

Updated Condo, 5 Mi To Disney, On-Site Water Park

3150 Paradox Circle #206, Kissimmee, United States Show map

The 1-bedroom Updated Condo, 5 Mi To Disney, On-Site Water Park Kissimmee villa is located within 7 km of Disney's Typhoon Lagoon Water Park and allows guests to enjoy surfing, mini golf, and cycling. More

From US$ 338 Book Now

Emerald Island Diamond On The Island

8578 Sunrise Key Drive, Kissimmee, United States Show map

Located around a 10-minute drive from Windsor Hills, the 6-bedroom Emerald Island Diamond On The Island Kissimmee villa has an outdoor swimming pool and is ideal for up to 16 guests. The availability… More

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Gorgeous 3Bd 2Ba Apt Close To Disney @ Storey Lake Orlando 208 3180

3180 Paradox Circle, Kissimmee, United States Show map

The 3-bedroom Gorgeous 3Bd 2Ba Apt Close To Disney @ Storey Lake Orlando 208 3180 Kissimmee villa is located around a 25-minute walk from the family-friendly Kissimmee Go-Karts and provides an… More

From US$ 123 Book Now

Shrek'S Hideout! - 5 Min From Disney!

2921 Sunset Lakes Boulevard, Kissimmee, United States Show map

Offering a sun deck and barbecue for guests' leisure, the 4-bedroom Shrek'S Hideout! - 5 Min From Disney! Kissimmee villa is situated 4.6 km from the 145-foot Tree of Life Sculpture. This property… More

From US$ 193 Book Now

Oasis With Heated Pool Marvel And Nemo Rooms Near Disney

8891 Geneve Ct, Kissimmee, Fl 34747, Usa, Kissimmee, United States Show map

Situated 3.8 km from Highgate Park Boulevard, the 5-bedroom Oasis With Heated Pool Marvel And Nemo Rooms Near Disney Kissimmee villa provides fitness classes, as well as a fitness centre for active… More

From US$ 473 Book Now

Lakeview Themed 2Br Condo Near Disney

3121 Paradox Circle, Kissimmee, United States Show map

Situated approximately a 10-minute drive from Local amusement Theme Park, the 2-bedroom Lakeview Themed 2Br Condo Near Disney Kissimmee villa provides fitness classes, as well as a fitness room for… More

From US$ 338 Book Now

3830 Premier Villa 6Bd Private Pool And Game Room

3830 Oakville Avenue, Kissimmee, United States Show map

Situated about 25 minutes on foot from Osceola County Welcome Center and History Museum, the 6-bedroom 3830 Premier Villa 6Bd Private Pool And Game Room Kissimmee features a terrace with views of the… More

From US$ 308 Book Now

Price Drop! Oct-Nov - 5Br - Pool & Bbq Windsor At Westside!

2411 Dubai Street, Kissimmee, United States Show map

Price Drop! Oct-Nov - 5Br - Pool & Bbq Windsor At Westside! Villa Kissimmee is located in the West Kissimmee district, 10 minutes' drive from Emerald Island Boulevard and features an outdoor swimming… More

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Amazing 6Br W Pvt Pool Game Room Near Disney

2838 Storey Cove Avenue, Kissimmee, United States Show map

Located about a 20-minute walk from Sam's Club, Amazing 6Br W Pvt Pool Game Room Near Disney Kissimmee villa has a swimming pool and is ideal for up to 13 guests. More

From US$ 489 Book Now

Relax In Ultimate Comfort With Pool & Bbq Area

4805 Dedication St, Kissimmee, Fl 34746, Usa, Kissimmee, United States Show map

Offering a Jacuzzi for a relaxing experience, Relax In Ultimate Comfort With Pool & Bbq Area Kissimmee villa is located 4 km from Old Town Shopping Mall. The 4-bedroom holiday home features… More

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5 Bedroom Villa With Private Pool, Close To Disney

4710 Ainsdale Walk, Kissimmee, United States Show map

Offering access to entertainment venues such as Xtreme Paintball Xperience, situated nearly a 25-minute walk away, the 5-bedroom 5 Bedroom Villa With Private Pool, Close To Disney Kissimmee can host… More

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Marvelous 3Bd Close To Disney W Gameroom At The Hub 3409

Tranquil Tr, Kissimmee, United States Show map

During the stay at Marvelous 3Bd Close To Disney W Gameroom At The Hub 3409 Kissimmee villa, guests can indulge in cycling and fisheries or visit Emerald Island Boulevard, located 2.7 km away. The 3… More

From US$ 168 Book Now

Stunning 5 Bd W Pool At Storey Lake Resort 2400

2400 Reading Trail, Kissimmee, United States Show map

The 5-bedroom Stunning 5 Bd W Pool At Storey Lake Resort 2400 Kissimmee villa is located approximately 6 km from Old Town Shopping Mall and provides cycling and fisheries for active guests. This… More

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Its A Dream Family Vacation Rental - Minutes From Disney

2973 Sunset Vista Boulevard, Kissimmee, United States Show map

Located merely 1.2 km from Emerald Island Boulevard, the 4-bedroom Its A Dream Family Vacation Rental - Minutes From Disney Kissimmee villa provides access to various tourist attractions in the… More

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Poinciana Paradise

2751 North Poinciana Boulevard, Kissimmee, United States Show map

The 3-bedroom Poinciana Paradise Kissimmee villa is located around 6 km from Disney's Typhoon Lagoon Water Park and provides a steam room, a Jacuzzi, and a sauna. Suitable for 6 guests, this property… More

From US$ 89 Book Now

Solara Villa With Themed Rooms And Private Pool

Fleming Mist Place 2170, Kissimmee, United States Show map

Located within 10 minutes' drive of Highlands Reserve Boulevard, the 4-bedroom Solara Villa With Themed Rooms And Private Pool Kissimmee has an outdoor swimming pool and is ideal for up to 12 guests. More

From US$ 388 Book Now

Redone Private Guesthouse Suite With Community Pool

2606 Judge Loop, Kissimmee, United States Show map

Along with access to such natural sites as Mindy O Waterpark, around 6 km away, the 1-bedroom Redone Private Guesthouse Suite With Community Pool Kissimmee villa offers an outdoor swimming pool. More

From US$ 113 Book Now

Three Bedrooms Townhome 3012

3012 Red Ginger Road, Kissimmee, United States Show map

Three Bedrooms Townhome 3012 Kissimmee villa is located in the West Kissimmee district, a 10-minute drive from Dinoland U.S.A and features an outdoor swimming pool as well as views of the lake. More

From US$ 97 Book Now

Smart Home Near Disney World, Silver Spurs Arena

2079 Heritage Key Boulevard, Kissimmee, United States Show map

The 3-bedroom Smart Home Near Disney World, Silver Spurs Arena Kissimmee is located 4.6 km from Spirit of the Swamp Airboat Rides and provides billiard for active guests. Featuring a Jacuzzi, this 3… More

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Perfect Vacation Home At Villa Domani Resort 168

168 Villa Domani Cir, Kissimmee, United States Show map

Located about 25 minutes on foot from Arnold Palmer Golf Course, the 4-bedroom Perfect Vacation Home At Villa Domani Resort 168 Kissimmee boasts a swimming pool with a hot tub. More

From US$ 104 Book Now

Beautiful Townhome Wprivate Pool 7 Mi To Disney

8911 Geneve Court, Kissimmee, United States Show map

Located a 10-minute drive from Highlands Reserve Boulevard, the welcoming Beautiful Townhome Wprivate Pool 7 Mi To Disney Kissimmee villa offers a game room for guests' leisure. Located 3.7 km from… More

From US$ 238 Book Now