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2026-04-23
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Vacation Rentals in Kissimmee

Luxury 6 Bedroom 5 Bath Pool Home 249

688 Whistling Straits Blvd, Kissimmee, United States View map

Nestled just 29 kilometers from the vibrant city of Kissimmee, the Luxury 6 Bedroom 5 Bath Pool Home 249 offers an exquisite retreat tailored for families and friends alike. This stunning abode… More

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Grh9284 - Solara Resort - 6 Bed 4 Baths Villa

1712 Caribbean View Terrace, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Grh9284 - Solara Resort - 6 Bed 4 Baths Villa Kissimmee is located a 25-minute walk from the Northeast Regional Park. Offering parking as well as Wi-Fi… More

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Grh9472 - Windsor Palms Resort - 4 Bed 3 Baths Villa

2209 Wyndham Palms Way, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Grh9472 - Windsor Palms Resort - 4 Bed 3 Baths Villa Kissimmee is located a 15-minute ride from the Windsor Hills. This villa features opportunities for… More

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Luxury 9 Bd 5 Bath With Private Pool And Spa 156

8910 Cabot Cliffs Drive, Kissimmee, United States View map

Discover the epitome of luxury at the remarkable Luxury 9 Bd 5 Bath With Private Pool And Spa 156, nestled just 29 kilometers from the heart of Kissimmee. This opulent retreat is designed for… More

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Disney Getaway Private Pool Themed Bedrooms. Book Now Dw5

2470 Santorini Dr, Kissimmee, United States View map

Offering beauty services and spa therapy for guests' leisure, Disney Getaway Private Pool Themed Bedrooms. Book Now Dw5 Kissimmee villa is situated approximately a 25-minute walk from the Rum Run. More

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Private Pool Townhome At Paradise Palms Resort

8873 Candy Palm Road, Kissimmee, United States View map

**The Paradise Palms is your ultimate retreat nestled in the heart of Kissimmee.** This enchanting destination offers an unparalleled blend of comfort and luxury, where the sun-kissed outdoors… More

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Luxury Villa 9Bdrms Poolgame Room-Champions Gate

671 Sticks St, Kissimmee, United States View map

Located approximately a 10-minute drive from ChampionsGate Golf Club, Luxury Villa 9Bdrms Poolgame Room-Champions Gate Kissimmee boasts a private swimming pool with a Jacuzzi and an indoor pool. More

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Casa 4Q + Sala De Jogos - 15 Min Da Disney

2941 Lucayan Harbour Circle, Kissimmee, United States View map

The 3-bedroom Casa 4Q + Sala De Jogos - 15 Min Da Disney Kissimmee is located approximately 25 minutes' walk from Fun Spot America Kissimmee and provides a hot tub and hot public baths. More

From US$ 155 Book Now

Esprit Luxurious Home

613 Jaybee Avenue, Kissimmee, United States View map

**Experience the Exquisite Charm of Esprit Luxurious Home** Nestled in the heart of Kissimmee, Esprit Luxurious Home offers an enchanting retreat just a 70-minute drive from the vibrant attractions… More

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Massive 4 000 Sqft Luxury Duplex

7770 Sandy Ridge Drive, Kissimmee, United States View map

**Welcome to the Massive 4.000 Sqft Luxury Duplex**, a magnificent retreat located just 23 kilometers from the heart of Kissimmee. This exquisite apartment is designed for those seeking an… More

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5 Bedrooms 4.5 Bathrooms Veranda Palms 2669 Sc

2669 Santosh Cove, Kissimmee, United States View map

Offering a location about 10 minutes by car from the Museum of Military History, 5 Bedrooms 4.5 Bathrooms Veranda Palms 2669 Sc Kissimmee villa gives access to various tourist spots in the area. More

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Conforto E Diversao No Champions Gate Resort

1240 Challenge Drive, Kissimmee, United States View map

During the stay at the 3-bedroom Conforto E Diversao No Champions Gate Resort Kissimmee villa, guests can indulge in a hot tub or visit Highlands Reserve Boulevard, located 3.2 km away. More

From US$ 257 Book Now

Wellerden At Reunion Resort Villa

1005 Castle Pines Ct., Kissimmee, United States View map

Welcome to Wellerden at Reunion Resort Villa, a stunning retreat located just 24 kilometers from the vibrant heart of Kissimmee. Nestled within the renowned Reunion Resort, this villa offers a… More

From US$ 502 Book Now

New Epic Family Luxury Retreat

1901 Nice Court, Kissimmee, United States View map

Located within a 3-km distance of Northeast Regional City Park, New Epic Family Luxury Retreat Villa Kissimmee provides access to an indoor swimming pool. Featuring an indoor pool, the Kissimmee… More

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Mickey'S Cozy Condo Retreat

2731 North Poinciana Boulevard, Kissimmee, United States View map

Staying at Mickey'S Cozy Condo Retreat Kissimmee villa, guests can visit the mile-long Kissimmee Go-Karts, which is nearly a 10-minute ride away. More

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6 Mi To Disney Gem With Pool And Spa In Kissimmee

Kissimmee, FL, 34747, Kissimmee, United States View map

Located in the West Kissimmee district of Kissimmee, the 3-bedroom 6 Mi To Disney Gem With Pool And Spa In Kissimmee villa is 3.1 km from the Emerald Island Boulevard and offers a hot tub. More

From US$ 245 Book Now

Dynamic 15 Bed With Character Bedrooms Pool, Spa! Villa

2413 Shanti Drive, Kissimmee, United States View map

**Welcome to Dynamic 15 Bed With Character Bedrooms Pool, Spa! Villa, an extraordinary retreat nestled just 9 km from the vibrant heart of Kissimmee.** Offering an eclectic atmosphere filled with… More

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2476 Shanti Drive 12Bed

2476 Shanti Drive, Kissimmee, United States View map

In the heart of Florida's vibrant Kissimmee, 2476 Shanti Drive 12Bed offers a serene retreat just 8 kilometers from the bustling downtown. A blend of modern decor and comfortable accommodations… More

From US$ 794 Book Now

Villa Tdm- Caribe Cove

9051 Treasure Trove Ln Unit 106 Bld 3, Kissimmee, United States View map

Nestled a 10-minute drive from Polo Park Golf Course, Villa Tdm- Caribe Cove Kissimmee entices guests to explore various tourist destinations nearby. More

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Spacious 12Br Disney Themed Home Pool/Spa/Bbq/Game

2528 Shanti Dr, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Spacious 12Br Disney Themed Home Pool/Spa/Bbq/Game Kissimmee is located 10 minutes' drive from Medieval Times Dinner & Tournament. The 12-bedroom villa… More

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Castle Street Memories

4958 Castle St E, Kissimmee, United States View map

**Castle Street Memories Villa Kissimmee is** your gateway to a tranquil retreat just 15 kilometers from the vibrant Kissimmee area. Nestled in the heart of Central Florida, this enchanting villa… More

From US$ 201 Book Now

201 Hb - Hideaway At Terraverde

201 Hideaway Beach Ln, Kissimmee, United States View map

**Welcome to 201 Hideaway at Terraverde**, a charming refuge nestled in the heart of Kissimmee, just 9 km from the bustling attractions of the area. This retreat offers a serene escape while being… More

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Disney Luxury Townhouse With Private Pool Themed Bedrooms. Book Now Dp61

2470 Santorini Dr, Kissimmee, United States View map

Offering a treatment room and an indoor pool for a relaxing experience, Disney Luxury Townhouse With Private Pool Themed Bedrooms. Book Now Dp61 Kissimmee villa is located a 10-minute ride from the… More

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Beautiful Cottage With Private Pool Near Disney With Margaritaville Resort & Island H20 Access - 8153Su

8153 Surf Street, Orlando, United States View map

Beautiful Cottage With Private Pool Near Disney With Margaritaville Resort & Island H20 Access - 8153Su Kissimmee is located a 10-minute drive from the 145 - foot Tree of Life Sculpture and invites… More

From US$ 1036 Book Now

1112 Luxurious Champions Gate Family Townhouse With Private Pool & Theme Park Access

1112 Challenge Drive, Kissimmee, United States View map

1112 Luxurious Champions Gate Family Townhouse With Private Pool & Theme Park Access Villa Kissimmee entices active guests with access to a fitness suite and is located approximately a 10-minute ride… More

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Luxery 5 Bed 5 Bath Home Near Disney With Resort Amenities

9115 Sommerset Hills Drive, Kissimmee, United States View map

Situated 4.5 km from Tuscan Hills Boulevard, Luxery 5 Bed 5 Bath Home Near Disney With Resort Amenities Kissimmee provides access to numerous tourist attractions in the area. More

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W451J - Glamorous Getaway With Themed Bedrooms At Reunion

614 Muirfield Loop, Kissimmee, United States View map

Welcome to the W451J - Glamorous Getaway With Themed Bedrooms At Reunion, an enchanting retreat nestled just 24 kilometers from the vibrant Kissimmee area and a convenient 45 kilometers from Orlando… More

From US$ 2735 Book Now

4 Bedrooms 3 Bathrooms Storey Lake 2621 Ss

2621 Scrapbook St, Kissimmee, United States View map

Set within the enchanting grounds of Storey Lake, the 4 Bedrooms-3 Bathrooms-Storey Lake 2621 Ss offers a perfect blend of comfort and modern living, making it an ideal retreat for families and… More

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Resort 9Mi From Disney Free Clubhouse Pool

8416 Blue Lagoon Drive, Kissimmee, United States View map

Welcome to the captivating Resort 9 Mi From Disney Free Clubhouse Pool, an inviting getaway perfectly situated just 60 minutes' drive from the enchanting attractions of Disney. Nestled in the vibrant… More

From US$ 151 Book Now

Paradise Cottage Near Disney With Margaritaville Resort & Island H2O Access - 8052Dr

8052 Dreamsicle Dr, Orlando, United States View map

Situated 2.8 km from the 145-foot Tree of Life Sculpture, the 2-bedroom Paradise Cottage Near Disney With Margaritaville Resort & Island H2O Access - 8052Dr Orlando provides access to numerous… More

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Dreamy 8 Bedroom Villa In Orlando6594

920 Desert Mountain Ct, Kissimmee, United States View map

Situated in the picturesque landscapes of Kissimmee, the Dreamy 8 Bedroom Villa in Orlando6594 redefines family retreat with an impeccable blend of comfort and luxury. This stunning villa is just 27… More

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4415Rh Townhouse 5 Bedrooms & 4 Bathrooms + Pool

4415 Scene Lane, Kissimmee, United States View map

Staying at 4415Rh Townhouse 5 Bedrooms & 4 Bathrooms + Pool Kissimmee villa, guests can visit the Dare 2 Escape|the Dare 2 Escape escape room, which is approximately 3 km away. More

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4718 Sleepy Hollow Drive

4718 Sleepy Hollow Drive, Kissimmee, United States View map

**Welcome to 4718 Sleepy Hollow Drive** Nestled in the heart of Kissimmee, just 12 kilometers from the vibrant pulse of downtown, 4718 Sleepy Hollow Drive is an idyllic retreat for families and… More

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Relaxing 1Br Pirate Themed Condo In Orlando Next To Disney With Pool View

5565 West Irlo Bronson Memorial Highway 540, Kissimmee, United States View map

**Welcome to the Relaxing 1Br Pirate Themed Condo In Orlando Next To Disney With Pool View**, your ideal oasis nestled just 14 kilometers from the vibrant heart of Kissimmee. This charming retreat… More

From US$ 179 Book Now

780Pb Luxury 5Bd Home

780 Pebble Beach Drive, Kissimmee, United States View map

**Welcome to the 780Pb Luxury 5Bd Home, a magnificent getaway nestled just 29 km from the vibrant heart of Kissimmee**. This luxurious residence epitomizes elegance and comfort, seamlessly combining… More

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Blissful Villa Near Disney With Margaritaville Resort & Island H20 Waterpark Access - 3109Cs

3109 Caribbean Soul Dr, Orlando, United States View map

Offering a location nearly a 25-minute walk from the A World of Orchids, the 2-bedroom Blissful Villa Near Disney With Margaritaville Resort & Island H20 Waterpark Access - 3109Cs Kissimmee gives… More

From US$ 378 Book Now

New Sparkling Court Retreat Pool Loft & Family Comforta

7400 Sparkling Court, Kissimmee, United States View map

Offering a location only 1 km from Arnold Palmer Golf Course, New Sparkling Court Retreat Pool Loft & Family Comforta Kissimmee villa gives access to various tourist spots in the area. More

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Orlando Oasis Homeaway Steps From Disney

2105 Malta Terrace, Kissimmee, United States View map

The 5-bedroom Orlando Oasis Homeaway Steps From Disney Kissimmee villa is located approximately 5 km from ChampionsGate Golf Club and offers guests to enjoy their evening on a terrace with outdoor… More

From US$ 376 Book Now

2920 Banana Palm

2920 Banana Palm Dr, Kissimmee, United States View map

**Welcome to the 2920 Banana Palm Villa, your idyllic retreat nestled just 34 kilometers from Kissimmee and 45 kilometers from the vibrant Orlando International Airport. This charming haven is… More

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Family Pool Home |Close To Disney/Universal/Epic

4894 Old Tampa Highway, Kissimmee, United States View map

Located within 6 km of Kissimmee Oaks Golf Course, Family Pool Home |Close To Disney/Universal/Epic Kissimmee provides access to various tourist attractions in the vicinity. More

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6Br Fun Villa - Game Room, Pool, Near Parks

910 Marcello Blvd, Kissimmee, United States View map

Featuring a fitness room for active guests, 6Br Fun Villa - Game Room, Pool, Near Parks Kissimmee is only an 8-minute walk from Give Kids The World Village Resort. More

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Exquisite, Spacious And Close To Disney 6 Bd Home #6Ws483

Dubai Street, Kissimmee, United States View map

**Experience Luxurious Leisure at Exquisite, Spacious And Close To Disney 6 Bd Home #6Ws483** Nestled just 32 kilometers from the vibrant heart of Kissimmee, Exquisite, Spacious And Close To Disney 6… More

From US$ 290 Book Now

Citrus Sunshine Villa Near Disney With Margaritaville Resort & Island H2O Access - 3049Cs

3049 Caribbean Soul Dr, Orlando, United States View map

Situated 25 minutes' walk from The Legends Golf Course, Citrus Sunshine Villa Near Disney With Margaritaville Resort & Island H2O Access - 3049Cs Kissimmee invites guests to relax at a terrace. More

From US$ 436 Book Now

Disney Getaway Private Pool Themed Bedrooms. Book Now Dw3

2470 Santorini Dr, Kissimmee, United States View map

During the stay at Disney Getaway Private Pool Themed Bedrooms. Book Now Dw3 Kissimmee villa, guests can indulge in an indoor pool or visit the Pandora, located 7 km away. This holiday home features… More

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Beautiful Condo On Reunion Resort And Spa Orlando Condo 5156

7608 Cabana Court Unit #202 (Building F), Kissimmee, United States View map

**Experience Luxurious Comfort at Beautiful Condo On Reunion Resort And Spa Orlando Condo 5156** Nestled within the scenic surroundings of the Reunion Resort, Beautiful Condo On Reunion Resort And… More

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Luxury Home With Themed Rooms, Air Hockey Near Disney With Waterpark & Resort Access At Encore Resort - 7699Gr

7699 Graben Street, Kissimmee, United States View map

Positioned in the heart of Celebration, the Luxury Home with Themed Rooms offers a unique and vibrant retreat, perfectly blending modern comforts with an enchanting atmosphere. This exquisite… More

From US$ 657 Book Now

7 Mi To Disney Condo With Pool And Hot Tub Access!

8718 Rain Forest Pl Unit A, Kissimmee, United States View map

To enjoy your vacation in Kissimmee, stay at the 126 m² 7 Mi To Disney Condo With Pool And Hot Tub Access! Kissimmee, which is 2.4 km from The Legends Golf Course and nearly a 25-minute walk from the… More

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

8068 Dreamsicle Drive, Orlando, United States View map

Situated 2.5 km from the Emerald Island Boulevard, the 3-bedroom Fiesta Siesta Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8068Dr Kissimmee invites guests to… More

From US$ 387 Book Now

Sandy Cottage! 3 Miles From Disney With Margaritaville Resort & Island H2O Access - 8080Dr

8080 Dreamsicle Drive, Orlando, United States View map

Located around a 25-minute walk from the Windsor Hills, the 3-bedroom Sandy Cottage! 3 Miles From Disney With Margaritaville Resort & Island H2O Access - 8080Dr Kissimmee gives access to various… More

From US$ 387 Book Now

Extravagant Home With Movie Theater, Private Pool And Waterpark & Resort Access At Encore Resort - 241Fl

241 Falls Dr, Kissimmee, United States View map

Situated in the enchanting community of Celebration, the Extravagant Home With Movie Theater, Private Pool And Waterpark & Resort Access At Encore Resort - 241Fl beckons those seeking a serene and… More

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