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2026-11-07
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Holiday Homes in Kissimmee

Private Pool Homes

1 Rental Way, Kissimmee, United States Show map

Private Pool Homes Kissimmee is located within 10 minutes' drive of Emerald Island Boulevard and provides a solarium. This Kissimmee holiday home boasts an aqua park, a sun deck, and a golf course… More

From US$ 137 Book Now

Margaritaville Cottages Orlando By Rentyl With H2O Waterpark

8000 Fins Up Circle, Kissimmee, United States Show map

Located around a 15-minute drive from Pandora, Margaritaville Cottages Orlando By Rentyl With H2O Waterpark Kissimmee provides pedicure, manicure, and facial treatments, along with a sauna. The… More

From US$ 10 Book Now

Stunning Townhouses 5 Minutes Away Disney!

Reading Trail, 2509, Kissimmee, United States Show map

Located around 25 minutes' walk from the miniature Pirates Island Adventure Golf, the 10-room Stunning Townhouses 5 Minutes Away Disney! Kissimmee villa features a heated pool, a Jacuzzi, ensuring a… More

From US$ 116 Book Now

Luxury Townhouses 4 And 5 Bedrooms 18 Minutes Away From Disney!

1168 Challenge Dr., Kissimmee, United States Show map

Situated 3.1 km from Highlands Reserve GC, the 6-room Luxury Townhouses 4 And 5 Bedrooms 18 Minutes Away From Disney! Kissimmee villa provides access to numerous tourist attractions in the area. More

From US$ 220 Book Now

Formosa Garden Pool Home

Formosa Gardens Boulevard, Kissimmee, United States Show map

Situated about 5 minutes' walk from Formosa Gardens Boulevard, the 2-room Formosa Garden Pool Home Kissimmee offers easy access to numerous tourist spots in the area. Providing guests with Wi-Fi and… More

From US$ 160 Book Now

Gorgeous 4 Bd W/ Pool At Champions Gate Resort 1020

1020 Leader St, Kissimmee, Florida 34747, Kissimmee, United States Show map

Located around a 10-minute drive from Tuscan Hills Boulevard, the 4-bedroom Gorgeous 4 Bd W/ Pool At Champions Gate Resort 1020 Kissimmee villa has a swimming pool and is ideal for up to 12 guests. More

From US$ 250 Book Now

Encore Resort And Water Park At Reunion By Rentyl

7635 Fairfax Drive, Kissimmee, United States Show map

Situated about 7 km from Disney's Blizzard Beach Water Park, Encore Resort And Water Park At Reunion By Rentyl Kissimmee villa offers guests to enjoy an aqua park, a sunbathing terrace, and a golf… More

From US$ 178 Book Now

Storey Lake Pool Mins To Disney 4Br Games

3081 Tom Sawyer Dr, Kissimmee, United States Show map

Situated 6 km from Disney's Typhoon Lagoon Water Park, Storey Lake Pool Mins To Disney 4Br Games Kissimmee villa is suitable for 12 guests and provides an outdoor swimming pool for additional… More

From US$ 239 Book Now

Luxury Champions Gate Condo, Resort-Style Retreat

1171 Drop Lane, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 3-bedroom Luxury Champions Gate Condo, Resort-Style Retreat Kissimmee villa is suitable for up to 8 people and is located about a 10-minute ride from Highlands… More

From US$ 186 Book Now

Berkley Lake Townhomes

1010 Park Ridge Circle, Kissimmee, United States Show map

Along with a heated pool, Berkley Lake Townhomes Kissimmee villa boasts a prime location only 1.4 km from Give Kids The World Village Resort, where guests can rejuvenate themselves. This Kissimmee… More

From US$ 120 Book Now

Stay At Hogwarts Harry Potter'S Home, Free Parking, Pets Allowed

2041 Lacie Jo Lane, Kissimmee, United States Show map

Offering a location 2.8 km from Mill Slough Park, the 4-bedroom Stay At Hogwarts Harry Potter'S Home, Free Parking, Pets Allowed Kissimmee gives access to various tourist spots in the area. This 3… More

From US$ 659 Book Now

Spacious 5Br Home With Pool Near Top Attractions

1140 Kingsbarn St, Kissimmee, United States Show map

The 5-bedroom Spacious 5Br Home With Pool Near Top Attractions Kissimmee entices active guests with access to a sports complex and is located just a 13-minute stroll from ChampionsGate Country Club… More

From US$ 252 Book Now

Upstay Resort Home W Private Pool Near Disney

Windermere Avenue 4953, Kissimmee, United States Show map

The 4-bedroom Upstay Resort Home W Private Pool Near Disney Kissimmee entices active guests with access to a fitness club and is located approximately a 10-minute ride from the creative Mortem Manor… More

From US$ 297 Book Now

Close To Disney & Other Theme Parks,Private Heated Poolspa, Bbq & Game Rm

591 Sweet Birdie Street, Kissimmee, United States Show map

Located nearly a 15-minute ride from Indian Ridge, the 6-bedroom Close To Disney & Other Theme Parks,Private Heated Poolspa, Bbq & Game Rm Kissimmee villa has an outdoor swimming pool and is ideal… More

From US$ 428 Book Now

Marvelous 7Bd/5Ba Family Friendly W/ Gameroom & Pool Close To Disney 1201

1201 Challenge Drive, Kissimmee, United States Show map

Marvelous 7Bd/5Ba Family Friendly W/ Gameroom & Pool Close To Disney 1201 Kissimmee villa, located a 6-minute walk from ChampionsGate Country Club Golf, can host up to 18 guests. More

From US$ 279 Book Now

Cozy Tiny Home Near Disney World & Orlando Parks!

2744 Camper Avenue, Kissimmee, United States Show map

Featuring an outdoor swimming pool, Cozy Tiny Home Near Disney World & Orlando Parks! Kissimmee is suitable for up to 5 people and is located 10 minutes' drive from Mill Slough Park. More

From US$ 90 Book Now

Renewed Luxury Townhouse With Private Pool

4808 Memories Lane, Kissimmee, United States Show map

The 4-bedroom Renewed Luxury Townhouse With Private Pool Villa Kissimmee offers proximity to nearby tourist spots, such as the outlet mall "Lake Buena Vista Factory Stores", situated approximately 25… More

From US$ 225 Book Now

Near Disney - 5Br Home- Games Pool Hot Tub & Bbq

Buccaneer Palm Road 2989, Kissimmee, United States Show map

Nestled around 6 km from Pandora, the 5-bedroom Near Disney - 5Br Home- Games Pool Hot Tub & Bbq Kissimmee is boasting a private swimming pool and barbecue for guests' enjoyment. Located about 10… More

From US$ 335 Book Now

Luxury 4-Bedroom Home With Private Pool, Jacuzzi, Ac, Wi-Fi, Cable Tv, 5 Minutes From Disney

2665 Oneida Loop, Kissimmee, United States Show map

Situated approximately 25 minutes on foot from A World of Orchids, the 4-bedroom Luxury 4-Bedroom Home With Private Pool, Jacuzzi, Ac, Wi-Fi, Cable Tv, 5 Minutes From Disney Kissimmee includes a… More

From US$ 276 Book Now

Family Resort - 6Br Mansion - Private Pool, Home Theater, Bbq And More

Ballo Drive 330, Kissimmee, United States Show map

Staying at Family Resort - 6Br Mansion - Private Pool, Home Theater, Bbq And More Kissimmee, guests can visit Medieval Times Dinner & Tournament, which is nearly a 25-minute walk away. More

From US$ 198 Book Now

Beautiful, Home In A Gated Community

255 Magical Way, Kissimmee, United States Show map

Beautiful, Home In A Gated Community Kissimmee is located within 25 minutes' walk of Crystalbrook Golf Course, giving access to various tourist spots nearby. More

From US$ 316 Book Now

Spacioustownhome 15 Min To Disney Private Pool-Bbq

8895 Geneve Ct, Kissimmee, United States Show map

The 5-bedroom Spacioustownhome 15 Min To Disney Private Pool-Bbq Kissimmee villa is located about 10 minutes' drive from Emerald Island Boulevard and provides a hot tub. The accommodation boasts an… More

From US$ 270 Book Now

Cozy 5 Bed, Wonderful Clubhouse, Close To Disney

1935 Majorca Drive, Kissimmee, United States Show map

Featuring an outdoor swimming pool, the 5-bedroom Cozy 5 Bed, Wonderful Clubhouse, Close To Disney Kissimmee villa is suitable for up to 10 people and is located 3.1 km from Highgate Park Boulevard. More

From US$ 191 Book Now

Cozykey Vacation Rentals

Central Location Only (Not Check In Location), Kissimmee, United States Show map

Staying at Cozykey Vacation Rentals Kissimmee villa, guests can easily reach Medieval Times Dinner & Tournament, located just 1.3 km away. More

From US$ 207 Book Now

Great 6Bedrooms Home In Kissimmee W Private Pool 8426

8426 Secret Key Cove, Kissimmee, United States Show map

Located in the West Kissimmee district, Great 6Bedrooms Home In Kissimmee W Private Pool 8426 is 25 minutes' walk from The Legends Golf Course and offers a Jacuzzi. The 6-bedroom holiday home… More

From US$ 265 Book Now

Casita Mi Encanto A Cozy & Spacious House, 4-Bedroom 3-Bath & Pool

240 Old Mill Circle, Kissimmee, United States Show map

Nestled 4.5 km from the Grassy Kissimmee Lakefront Waterfront Park, the 4-bedroom Casita Mi Encanto A Cozy & Spacious House, 4-Bedroom 3-Bath & Pool Kissimmee villa is boasting an aqua park, a… More

From US$ 257 Book Now

The Villas At Seven Dwarfs - 2603 Amazing Luxury Villa - Near Disney - Water Park

2603 Gala Road South, Kissimmee, United States Show map

The Villas At Seven Dwarfs - 2603 Amazing Luxury Villa - Near Disney - Water Park Kissimmee is located a 25-minute walk from Fantasy Surf and invites guests to join ping-pong, billiard, and fisheries… More

From US$ 174 Book Now

Townhome With Private Pool, Bbq & Free Waterpark

2030 Majorca Drive, Kissimmee, United States Show map

Situated approximately a 10-minute drive from West Gate Flea Market, the 5-bedroom Townhome With Private Pool, Bbq & Free Waterpark Kissimmee villa includes a swimming pool, as well as a hot tub to… More

From US$ 235 Book Now

Beautiful Family Villa - Pool And Hot Tub - Near Disney World

4274 Paragraph Drive, Kissimmee, United States Show map

Nestled around 7 km from Old Town Shopping Mall, the 5-bedroom Beautiful Family Villa - Pool And Hot Tub - Near Disney World Kissimmee is boasting an aqua park and a golf course for guests' enjoyment… More

From US$ 276 Book Now

Near Disney Private Hot Tub Resort Pools

3023 Red Ginger Road, Kissimmee, United States Show map

Featuring a car park, the 3-bedroom Near Disney Private Hot Tub Resort Pools Kissimmee villa is located in the West Kissimmee district of Kissimmee and approximately 10 minutes' drive from such… More

From US$ 153 Book Now

Fully Renovated, Quiet, Spacious Disney Themed Pool Home With Office

1037 Lake Berkley Drive, Kissimmee, United States Show map

Fully Renovated, Quiet, Spacious Disney Themed Pool Home With Office Kissimmee is located a 25-minute walk from Shingle Creek Regional Park and provides an outdoor swimming pool, ensuring a relaxing… More

From US$ 274 Book Now

Chic 5Bed Retreat, Perfect For Family Getaway

8943 Play Through Dr, Kissimmee, United States Show map

During the stay at the welcoming Chic 5Bed Retreat, Perfect For Family Getaway Villa Kissimmee, guests can indulge in a hot tub or visit Tuscan Hills Boulevard, located 4.2 km away. Located in an… More

From US$ 260 Book Now

Chic 5Bed Home With Themed Rooms

9009 Play Through Dr, Kissimmee, United States Show map

The 5-bedroom Chic 5Bed Home With Themed Rooms Kissimmee is located around 5 km from Highgate Park Boulevard and provides a Jacuzzi. This holiday home hosts up to 14 guests and provides them with… More

From US$ 289 Book Now

Island 1

1473 Pine Needle Lane, Kissimmee, United States Show map

Offering an outdoor swimming pool, the 3-bedroom Island 1 Villa Kissimmee is located nearly 5 minutes' walk from Mill Slough Park and is ideal for up to 6 guests. Providing guests with Wi-Fi and… More

Book Now

Spacious 5Br Family Home Near Disney

2825 Roccella Court, Kissimmee, United States Show map

Featuring a swimming pool, Spacious 5Br Family Home Near Disney Kissimmee is suitable for up to 11 people and is located 15 minutes' drive from Pandora. Providing guests with Wi-Fi and parking, the 5… More

From US$ 237 Book Now

Gorgeous 5Bed Th Close To Disney, Water Park

1102 Kingsbarn St, Kissimmee, United States Show map

Offering a hot tub for a relaxing experience, the welcoming Gorgeous 5Bed Th Close To Disney, Water Park Kissimmee villa is located 3.5 km from Highlands Reserve Boulevard. Providing guests with Wi… More

From US$ 229 Book Now

Disney Dream With Hot Tub, Pool, Xbox, Games Room, Lakeview, 10 Min To Disney, Clubhouse

182 Hideaway Beach Lane, Kissimmee, United States Show map

Located approximately 6 km from Museum of Military History, the 7-bedroom Disney Dream With Hot Tub, Pool, Xbox, Games Room, Lakeview, 10 Min To Disney, Clubhouse Kissimmee villa offers live… More

From US$ 356 Book Now

7988 Spacious 5Bd Disney Vacation Home With Pool

7988 Formosa Valley Place 7988, Kissimmee, United States Show map

The 5-bedroom 7988 Spacious 5Bd Disney Vacation Home With Pool Kissimmee can host up to 12 guests, boasting a prime location 4.7 km from iconic cultural attractions such as the 145 - foot Tree of… More

From US$ 164 Book Now

8 Bedroom Home Inside The Best Resort In Orlando!

8890 Cabot Cliffs Drive, Kissimmee, United States Show map

Situated around a 25-minute stroll from ChampionsGate Golf Club, the 8-bedroom 8 Bedroom Home Inside The Best Resort In Orlando! Kissimmee includes an outdoor swimming pool, as well as a Jacuzzi to… More

From US$ 321 Book Now

Large Villa, Private Poolgame Roommovie Theater

781 Sticks Street, Kissimmee, United States Show map

Nestled 10 minutes by car from Highlands Reserve Boulevard, the welcoming Large Villa, Private Poolgame Roommovie Theater Kissimmee is boasting water slides, a patio, and playground for guests'… More

From US$ 268 Book Now

Magical Themed Home - Disney 15 Min

4382 Rhyme Street, Kissimmee, United States Show map

The 6-bedroom Magical Themed Home - Disney 15 Min Kissimmee is located approximately 25 minutes' walk from Give Kids The World Village Resort and provides a Jacuzzi. With a maximum capacity of 14… More

From US$ 626 Book Now

Winterfield At Disney 9350

9350 Sommerset Hills Drive, Kissimmee, United States Show map

Staying at Winterfield At Disney 9350 Kissimmee villa, guests can easily reach Rum Run, located about a 10-minute ride away. More

From US$ 362 Book Now

25% Off 4Br Pool Villagame Room

1589 Oak Hill Trail, Kissimmee, United States Show map

Featuring a swimming pool, the 4-bedroom 25% Off 4Br Pool Villagame Room Kissimmee villa is suitable for up to 8 people and is located 3.9 km from Reunion Resort Water Park. Providing guests with Wi… More

From US$ 359 Book Now

Townhome W Pool Near Disney & Orlando Attractions

8988 Cuban Palm Road, Kissimmee, United States Show map

Situated 4.7 km from Highlands Reserve Boulevard, the 4-bedroom Townhome W Pool Near Disney & Orlando Attractions Kissimmee villa offers guests to enjoy a sunbathing terrace and a patio. Nestled in… More

From US$ 245 Book Now

4Br Disney Area Villa - Private Pool - Resort Amenities - Sleeps 10

8971 Coco Palm Road, Kissimmee, United States Show map

Situated approximately 5 minutes' walk from Paradise Palms Boulevard, the 4-bedroom 4Br Disney Area Villa - Private Pool - Resort Amenities - Sleeps 10 Kissimmee offers quick access to numerous city… More

From US$ 671 Book Now

Gorgeous 5 Bd W/ Pool Close To Disney @ Champions Gate 948

Leader Street, Kissimmee, United States Show map

During the stay at Gorgeous 5 Bd W/ Pool Close To Disney @ Champions Gate 948 Kissimmee villa, guests can indulge in cycling and fisheries or visit Highlands Reserve Boulevard, located 3.1 km away. More

From US$ 207 Book Now

8937 Paradise Palms 4Br Townhome With Private Pool Near Clubhouse

8937 Candy Palm Road, Kissimmee, United States Show map

Featuring a swimming pool, 8937 Paradise Palms 4Br Townhome With Private Pool Near Clubhouse Kissimmee villa is suitable for up to 10 people and is located 6 km from Pandora. Offering a Jacuzzi, the… More

From US$ 195 Book Now

6Br 6Bath Pvt Home Pool 10Min Disney 3282Ft

2962 Buccaneer Palm Rd, Kissimmee, United States Show map

Featuring an aqua park, a sun deck, and a golf course for added enjoyment, the 6-bedroom 6Br 6Bath Pvt Home Pool 10Min Disney 3282Ft Kissimmee is located nearly 5 minutes' walk from Paradise Palms… More

From US$ 641 Book Now

Deluxe Villas Resort At Seven Dwrafs - Close To Disney

2600 Lodi Circle. 106 01, Kissimmee, United States Show map

Offering a solarium and a Jacuzzi, the 5-room Deluxe Villas Resort At Seven Dwrafs - Close To Disney Kissimmee is situated 600 metres from the outlet mall "Lake Buena Vista Factory Stores" and can… More

From US$ 183 Book Now

5Br 5Bath Pvt Home Bbq Pool 15Min Disney 3056Ft

3890 Oakville Ave, Kissimmee, United States Show map

Located around a 25-minute walk from Shingle Creek Regional Park, the 5-bedroom 5Br 5Bath Pvt Home Bbq Pool 15Min Disney 3056Ft Kissimmee offers fitness classes, as well as a fitness room for active… More

From US$ 306 Book Now