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2026-06-08
2026-06-09
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Kissimmee holiday rentals

3 Bedroom 2.5 Bathroom Encantada Resort 3014 Wo

3014 White Orchid Road, Kissimmee, United States View map

Staying at the 2-bedroom 3 Bedroom 25 Bathroom Encantada Resort 3014 Wo Kissimmee villa, guests can visit Mystic Dunes Golf Club at Mystic Dunes Resort, which is approximately 4 km away. More

From US$ 143 Book Now

W429 - Bohemian Chic Villa With Themed Bedrooms At Reunion

711 Golden Bear Drive, Kissimmee, United States View map

Situated in the heart of Kissimmee, the Bohemian Chic Villa provides an exquisite retreat for those seeking a unique blend of luxury and comfort. This stunning property is only 23 kilometers from the… More

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Lovely 2Br Lakeview Condo With 2 Clubhouses

Paradox Circle 3191, Kissimmee, United States View map

Positioned just 12 kilometers from the vibrant Kissimmee community, the Lovely 2Br Lakeview Condo With 2 Clubhouses offers a serene escape infused with modern comforts. This exceptional lakeside… More

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9 Bedrooms 5 Bathrooms Storey Lake 4320Pw

4320 Prologue Way, Kissimmee, United States View map

The 5-bedroom 9 Bedrooms 5 Bathrooms Storey Lake 4320Pw Kissimmee villa is located around 25 minutes' walk from the adventure-themed Congo River Golf, giving access to various tourist spots nearby. More

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Disney Getaway Private Pool Themed Bedrooms. Book Now Dw10

2470 Santorini Dr, Kissimmee, United States View map

Disney Getaway Private Pool Themed Bedrooms. Book Now Dw10 Kissimmee villa is located around 10 minutes by car from the Emerald Island Boulevard and provides an indoor pool. This Kissimmee holiday… More

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Windsor Palm 3 Bed Condo

2300 Silver Palm Drive Unit 301, Kissimmee, United States View map

The splendid Windsor Palm 3 Bed Condo is a luxurious retreat nestled just 30 km from the vibrant heart of Kissimmee. Offering a perfect blend of modern comfort and unparalleled convenience, this… More

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Your Home Away From Home At Windsor At Westside

8830 Macapa Dr, Kissimmee, United States View map

During the stay at Your Home Away From Home At Windsor At Westside Kissimmee, guests can indulge in an indoor pool or visit the Windsor Hills, located 4.5 km away. Offering a car park as well as Wi… More

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W486 - The Dream Getaway

7453 Gathering Dr., Kissimmee, United States View map

Welcome to W486 - The Dream Getaway Villa, a serene oasis nestled just 21 kilometers from the vibrant heart of Kissimmee, Florida. This luxurious escape offers guests unparalleled access to Orlando's… More

From US$ 297 Book Now

3Bd Townhome With Pool 12Mi To Disney And Universal

3146 Britannia Boulevard, Kissimmee, United States View map

Welcome to 3Bd Townhome With Pool 12Mi To Disney And Universal Kissimmee, an oasis of comfort and modern convenience just 12 miles from the enchantment of Disney and Universal Studios. This charming… More

From US$ 196 Book Now

Luxury 4 Bedroom 3 Bath Pool Home 115

260 Ocean Course Av, Kissimmee, United States View map

Featuring a private pool for guests' relaxation, Luxury 4 Bedroom 3 Bath Pool Home 115 Kissimmee is located nearly a 10-minute ride from the Rum Run. More

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Treasure Hunt Retreat Home

8531 Sunrise Key Drive, Kissimmee, United States View map

**Welcome to Treasure Hunt Retreat Home, a serene getaway nestled just 60 minutes from the bustling heart of Kissimmee.** This exquisite retreat seamlessly combines modern comfort with tranquil… More

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Casa9 Quartos P/ Familia+Temas C/ Piscina

4533 Target Boulevard, Kissimmee, United States View map

Featuring a private pool for guests' relaxation, Casa9 Quartos P/ Familia+Temas C/ Piscina Kissimmee villa is located around a 10-minute ride from Medieval Times Dinner & Tournament. More

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Flash 20 Off Townhome At Reunion Resort

844 Driving Range Court, Kissimmee, United States View map

Situated within the renowned Reunion Resort, the Flash 20 Off Townhome serves as an idyllic retreat, just 27 km from the vibrant attractions of Kissimmee. This beautifully appointed accommodation… More

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Grh9352 - Paradise Palms Resort - 4 Bed 3 Baths Townhome

8975 Majesty Palm Road, Kissimmee, United States View map

Offering a sauna for a relaxing experience, Grh9352 - Paradise Palms Resort - 4 Bed 3 Baths Townhome Kissimmee villa is located a 15-minute drive from the Avatar Flight of Passage. Offering parking… More

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Luxurious Home Near Disney With Game Room And Waterpark & Resort Access At Encore Resorts Reunion - 371Fl

371 Falls Dr,, Kissimmee, United States View map

Disney-Adjacent with Private Pool & Resort Amenities, a serene oasis nestled in the heart of Central Florida's enchanting Celebration community. This luxurious retreat provides an unforgettable… More

From US$ 359 Book Now

Reunion Dream Oasis-Tt482

1173 Grand Traverse Parkway, Kissimmee, United States View map

The 7-bedroom Reunion Dream Oasis-Tt482 Villa Kissimmee is located 3.7 km from the Indian Ridge and provides a sauna. More

From US$ 1355 Book Now

Grand 15-Bedroom Villa -Magical Themes, Pool & Game Loft, Lakeview

4041 Sonoma Boulevard, Kissimmee, Florida 34741, United States, Kissimmee, United States View map

**Experience the Enchantment of Grand 15-Bedroom Villa - Magical Themes, Pool & Game Loft, Lakeview** More

From US$ 2285 Book Now

Resort Home: Game Room, Pool, Near Disney

2874 Stanza Court, Kissimmee, United States View map

The 5-bedroom Resort Home: Game Room, Pool, Near Disney Kissimmee is located about 10 minutes' drive from Shingle Creek Regional Park and provides cycling, billiards, and fishing for active guests. More

From US$ 402 Book Now

Solara Resort Vacation Home 6Beds

1840 Caribbean View Terrace, Kissimmee, United States View map

Welcome to Solara Resort Vacation Home 6Beds, a captivating retreat situated just 60 minutes' drive from the enchanting city of Kissimmee. This luxurious vacation home seamlessly blends the comfort… More

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Cheerful Villa Near Disney With Margaritaville Resort And Island H20 Waterpark Access - 2913Cs

2913 Caribbean Soul Dr, Kissimmee, United States View map

Featuring a swimming pool for guests' relaxation, the 3-bedroom Cheerful Villa Near Disney With Margaritaville Resort And Island H20 Waterpark Access - 2913Cs Kissimmee is located within 25 minutes'… More

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Delight Indoor 10Bed Free Acces To Resort

2105 Malta Terrace, Kissimmee, United States View map

**Discover the Allure of Delight Indoor 10Bed Free Access To Resort** Ideally located, this enchanting resort serves as a gateway to the myriad attractions of Central Florida. More

From US$ 264 Book Now

Family Retreat Near Disney With Private Pool

La Isla Drive 8646, Kissimmee, United States View map

Family Retreat Near Disney With Private Pool Kissimmee villa is located 5 km from the Dinosaur attraction and invites guests to enjoy a patio. More

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Best Location In Solara Resort

9001 Egret Mills Terrace, Kissimmee, United States View map

Welcome to the Best Location In Solara Resort Kissimmee, an exquisite retreat that perfectly blends luxury and convenience. Nestled just 32 kilometers from Kissimmee and approximately 50 kilometers… More

From US$ 305 Book Now

Disney Getaway Private Pool Themed Bedrooms. Book Now Dw12

2470 Santorini Dr, Kissimmee, United States View map

Nestled 2.9 km from Highlands Reserve Boulevard, Disney Getaway Private Pool Themed Bedrooms. Book Now Dw12 Kissimmee villa is boasting beauty services and spa therapy for guests' enjoyment. Located… More

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Brand New House Private Lake View 3009 Protagonist Home

3009 Protagonist, Kissimmee, United States View map

Brand New House Private Lake View 3009 Protagonist Home Kissimmee is located 3.6 km from Fun Spot America Kissimmee and provides a hot tub. More

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Et009 - Artistic Townhouse With Games Room At Reunion

836 Driving Range Ct, Kissimmee, United States View map

**Experience Comfort at the Artistic Townhouse** Welcome to the Artistic Townhouse, a charming retreat perfectly situated in Reunion, just 27 km from the vibrant heart of Kissimmee. More

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Spacious 3Br Home In Champions Gate Near Disney Chg106

1081 Splash Shot Pl, Kissimmee, United States View map

The 2-bedroom Spacious 3Br Home In Champions Gate Near Disney Chg106 Kissimmee is located 3.2 km from Highlands Reserve Boulevard and provides mini golf and ping pong for active guests. Providing… More

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Casa De Kissimmee Sleeps Up To 13 Guests

8925 Cuban Palm Rd, Kissimmee, United States View map

Escape to the enchanting **Casa De Kissimmee Sleeps Up To 13 Guests**, a charming villa located just 34 km from the heart of Kissimmee, Florida. This exquisite retreat caters to families and large… More

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8157 Fan Palm

8157 Fan Palm Way, Kissimmee, United States View map

**Welcome to 8157 Fan Palm Villa, a luxurious retreat nestled in the heart of Kissimmee, just 30 kilometers from the vibrant attractions of the town and a scenic 45 kilometers from Orlando… More

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Daisy'S Den - Five Bedroom Home

8088 Santee Drive, Kissimmee, United States View map

**Welcome to Daisy's Den - Five Bedroom Home, a luxurious retreat nestled just 30 km from the enchanting city of Kissimmee.** This charming property seamlessly combines comfort and elegance, making… More

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Cozy Family Retreat Minutes From Disneyland

7407 Excitement Drive, Reunion Kissimmee, Unit A Fl, 34747, Us, Kissimmee, United States View map

The Cozy Family Retreat Minutes From Disneyland is a charming getaway just 22 km from the heart of Kissimmee. This delightful haven combines comfort and convenience, making it an ideal destination… More

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3 Bd 2 Ba West Lucaya 3214 Cp

3214 Cupid Place, Kissimmee, United States View map

Staying at 3 Bd 2 Ba West Lucaya 3214 Cp Kissimmee villa, guests can visit Disney's Blizzard Beach Water Park, which is approximately a 15-minute ride away. More

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Relaxing Getaway In Emerald Island Near Disney

8518 Crystal Cove Loop, Kissimmee, United States View map

Set within the enchanting Emerald Island community, the Relaxing Getaway In Emerald Island Near Disney invites guests to bask in its captivating charm while being just 31 km from the vibrant heart of… More

From US$ 297 Book Now

Sun-Filled 7 Bdrm Haven With Sports Themed Game Room At Reunion

325 Muirfield Loop, Kissimmee, United States View map

**Welcome to the Sun-Filled 7 Bdrm Haven with Sports Themed Game Room at Reunion**, a delightful retreat that seamlessly blends luxury and comfort for unforgettable family getaways. Nestled just 27… More

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Windsor At Westside 7Bd Hm Pool-2112Mw Home

2112 Morocco Way, Kissimmee, United States View map

**Experience Luxurious Family Retreat at Windsor at Westside** Ideal for families, the property's location makes it easy to explore the enchanting attractions of Kissimmee and beyond. More

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Stylish Townhome With Splash Pool, Wi-Fi- 8206Sa

1612 Carey Palm Cir, Kissimmee, United States View map

The Stylish Townhome With Splash Pool, Wi-Fi- 8206Sa is an enchanting retreat nestled just 32 km from the vibrant heart of Kissimmee. This charming townhome offers a delightful blend of modern… More

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3070 Gatsby

3070 Gatsby Street, Kissimmee, United States View map

**3070 Gatsby Villa is a charming retreat nestled in the heart of Kissimmee.** Just a short 20-minute drive from the bustling attractions of Kissimmee, this delightful villa offers the perfect… More

From US$ 240 Book Now

Grh9245 - Storey Lake Resort - 4 Bed 3 Baths Townhome

4805 Brier Rose Lane, Kissimmee, United States View map

Offering a location 4.3 km from Medieval Times Dinner & Tournament, Grh9245 - Storey Lake Resort - 4 Bed 3 Baths Townhome Kissimmee villa gives access to various tourist spots in the area. More

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Disney Getaway Private Pool Themed Bedrooms. Book Now Dw51

2470 Santorini Dr, Kissimmee, United States View map

Situated in the West Kissimmee district of Kissimmee, 4.9 km from Mystic Dunes Golf Club at Mystic Dunes Resort, Disney Getaway Private Pool Themed Bedrooms. Book Now Dw51 Kissimmee villa comes with… More

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Perfect Retreat With Incredible Resort

1943 Majorca Drive, Kissimmee, United States View map

Perfect Retreat With Incredible Resort Kissimmee villa entices active guests with access to a fitness studio and is located within 25 minutes' walk of Northeast Regional City Park. Featuring a patio,… More

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Spacious 4-Bedroom Family Retreat Near Disneyland!

8900A Shine Drive, Kissimmee, United States View map

**Spacious 4-Bedroom Family Retreat Near Disneyland!** Offers a welcoming atmosphere perfect for families seeking adventure and relaxation. Nestled in the heart of Kissimmee, this charming retreat is… More

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Fun & Fancy Villa

1209 Challenge Drive, Kissimmee, United States View map

Fun & Fancy Villa Kissimmee is located 4.7 km from the Rum Run and provides cycling for active guests. Located 10 minutes' drive from Highlands Reserve GC, this 5-bedroom villa provides Wi-Fi and… More

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Upscale 8 Bdrm Villa With Home Theater At Reunion

920 Golden Bear Drive, Kissimmee, United States View map

The Upscale 8-Bedroom Villa with Home Theater at Reunion is an exquisite retreat situated in the heart of Kissimmee. This luxurious accommodation is designed to provide guests with an unforgettable… More

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6Br Luxury Home - Private Pool Hot Tub And Bbq

Marcello Boulevard 358, Kissimmee, United States View map

Welcome to 6Br Luxury Home - Private Pool Hot Tub And BBQ, where modern elegance meets the comforts of home. Nestled just 8 km from the vibrant heart of Kissimmee, this exquisite retreat offers an… More

From US$ 399 Book Now

3 Bedrooms 2.5 Bathrooms Lake Berkley 1109Pr

1109 Park Ridge Circle, Kissimmee, United States View map

Located a 16-minute walk from Medieval Times Dinner & Tournament, 3 Bedrooms 25 Bathrooms Lake Berkley 1109Pr Kissimmee villa gives access to various tourist sites in the vicinity. More

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Beautiful Home Close To Theme Parks With Private Pool, Ac & W/D - Dog-Friendly

4958 Castle St E, Kissimmee, United States View map

Beautiful Home Close To Theme Parks With Private Pool, Ac & W/D - Dog-Friendly Kissimmee is located 15 minutes' drive from Kissimmee Oaks Golf Course and invites guests to enjoy a patio. More

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Family 5Br Retreat Near Disney

4451 Scene Ln, Kissimmee, United States View map

Offering an indoor pool for a relaxing experience, Family 5Br Retreat Near Disney Kissimmee villa is located a 10-minute drive from the Museum of Military History. More

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Beautiful 5Bed Home With Free Resort Access 4817

4817 Love Storey Ln, Kissimmee, United States View map

Nestled just a scenic 20-minute drive from the vibrant heart of Kissimmee, the Beautiful 5Bed Home With Free Resort Access 4817 is the perfect retreat for families seeking both comfort and adventure.… More

From US$ 209 Book Now

Wondara Retreat - Golf Sim - Star Wars-Frozen-Lego Batman-Pool W-Slide By Disney

745 Desert Mountain Court, Kissimmee, United States View map

Situated nearly a 10-minute drive from the Windsor Hills, Wondara Retreat - Golf Sim - Star Wars-Frozen-Lego Batman-Pool W-Slide By Disney Kissimmee villa offers a private pool, a spa centre for… More

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Le572X Liberty Plaza

7572 Excitement Drive, Kissimmee, United States View map

**Welcome to Le572X Liberty Plaza**, an exquisite retreat nestled in the enchanting locale of Kissimmee, just 23 kilometers from the vibrant heart of Orlando. This gem offers a blend of contemporary… More

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