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2026-02-15
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Kissimmee holiday rentals

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

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Disney Getaway Private Pool Themed Bedrooms. Book Now Dw51

2470 Santorini Dr, Kissimmee, United States View map

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Perfect Retreat With Incredible Resort

1943 Majorca Drive, Kissimmee, United States View map

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Fun & Fancy Villa

1209 Challenge Drive, Kissimmee, United States View map

**Welcome to Fun & Fancy Villa Kissimmee**, an ideal retreat nestled just 28 kilometers from the vibrant heart of Kissimmee and a short drive from the magic of Orlando. Perfect for families 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 25 Bathrooms Lake Berkley 1109Pr

1109 Park Ridge Circle, Kissimmee, United States View map

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Family 5Br Retreat Near Disney

4451 Scene Ln, Kissimmee, United States View map

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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

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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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Modern 7 Bdrm Villa With Games Room At Reunion

1141 Castle Pines Ct., Kissimmee, United States View map

**Experience Luxurious Comfort at the Modern 7 Bdrm Villa with Games Room at Reunion** Nestled just 15 km from the bustling Kissimmee Value Outlet Shops, the Modern 7 Bdrm Villa with Games Room at… More

From US$ 1134 Book Now

Compass Point Villa S

3185 Tocoa Circle, Kissimmee, United States View map

**Welcome to the Compass Point Villa S, a luxurious getaway nestled just 13 km from the vibrant heart of Kissimmee and approximately 35 km from the bustling Orlando International Airport. Velvety… More

From US$ 125 Book Now

Villa Crayson

8800 Crayson Court, Kissimmee, United States View map

Villa Crayson Kissimmee is a luxurious retreat set against the enchanting backdrop of Florida's vibrant attractions. Located just 35 kilometers from the bustling heart of Kissimmee, this exquisite… More

From US$ 262 Book Now

Villa Crayson Home

8800 Crayson Court, Kissimmee, United States View map

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Last Minute Disney Luxury Townhouse With Private Pool. Book Now Slr557

4184 Paragraph Dr, Kissimmee, United States View map

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Lake View Pool Home Near Disney - 5Br 4Ba

8855 Candy Palm Road, Kissimmee, United States View map

Welcome to the Lake View Pool Home Near Disney, where the charm of Kissimmee meets modern luxury. Nestled just 34 kilometers from the vibrant heart of Kissimmee, this stunning retreat offers a… More

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Stunning 4Bd W Pool Gameroom Solara Resort 9008

9008 Egret Mills Terrace, Kissimmee, United States View map

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Go19 - Champions Gate

1220 Challenge Dr, Kissimmee, United States View map

**Discover the Luxury of Go19 - Champions Gate Villa Kissimmee** Located within close proximity to iconic attractions and theme parks, guests will find themselves perfectly positioned to explore the… More

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7 Mi To Usta Waterfront Tennis House With Yard!

3069 Sangria St, Kissimmee, United States View map

Welcome to the delightful 7 Mi To Usta Waterfront Tennis House With Yard!, A charming retreat just a short 20-minute drive away from Kissimmee. Nestled in a serene setting, this property offers a… More

From US$ 344 Book Now

Tg220T Heritage Rock Spring

1220 Grand Traverse Parkway, Kissimmee, United States View map

**Welcome to Tg220T Heritage Rock Spring** - an enchanting retreat nestled just 25 km from the vibrant heart of Kissimmee, offering a sanctuary amid Florida's natural beauty. This captivating haven… More

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Modern Storey Lake Resort Disney Orlando 3161-305

3161 Paradox Circle Apt 305, Kissimmee, United States View map

**Discover Modern Elegance at Modern Storey Lake Resort Disney Orlando 3161-305** Nestled just 12 km from the vibrant streets of Kissimmee, the Modern Storey Lake Resort Disney Orlando 3161-305… More

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Homestead Holly

7550 Gathering Drive, Kissimmee, United States View map

Set in the enchanting region of Kissimmee, Homestead Holly is a serene escape just a 40-minute drive from Orlando's bustling attractions. This charming haven boasts a captivating retreat designed for… More

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9Br Pool Home At Solara Resort Near Disney

1799 Caribbean View Terrace, Kissimmee, United States View map

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8963 Solara Resort 6Bdrs

8963 Amelia Downs Trail, Kissimmee, United States View map

The exquisite 8963 Solara Resort 6Bdrs is an ideal haven situated just 32 km from the vibrant heart of Kissimmee. This stunning retreat perfectly blends luxury and comfort, making it a prime choice… More

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4 Bedrooms 3 Bathrooms Storey Lake 4863 Rc

4863 Romeo Circle, Kissimmee, United States View map

**Welcome to Storey Lake, Your Ideal Home Away from Home** Nestled in the vibrant area of Kissimmee, the 4 Bedroom-3 Bathroom Storey Lake 4863 Rc offers a perfect blend of comfort and convenience. More

From US$ 172 Book Now

1961 Majorca Dr Kissimmee

1961 Majorca Drive, Kissimmee, United States View map

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8496 Resort 3Br Condo By Disney World Orlando

8496 Crystal Cove Loop, Kissimmee, United States View map

Welcome to the splendid 8496 Resort 3Br Condo By Disney World Orlando, a quintessential retreat designed for families and friends craving adventure and relaxation. Nestled a mere 31 km from the… More

From US$ 314 Book Now

Ultimate 9-Bed Luxury Retreat - Movie Theater, Game Room, Pool, Spa & Themed Bedrooms In Resort Paradise

9031 Sunset Palms Terrace, Kissimmee, United States View map

The 6-bedroom Ultimate 9-Bed Luxury Retreat - Movie Theater, Game Room, Pool, Spa & Themed Bedrooms In Resort Paradise Kissimmee villa is situated around 25 minutes' walk from Highlands Reserve… More

From US$ 360 Book Now

Family Oasis With Pool, Near Disney

751 Pebble Beach Dr, Kissimmee, Fl 34747, Usa, Kissimmee, United States View map

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From US$ 365 Book Now

9 Bedrooms 5 Bathrooms Champions Gate 8892 Cd

8892 Cabot Cliffs Drive, Kissimmee, United States View map

**Welcome to Champions Gate 8892 Cd, a luxurious escape designed for those seeking both relaxation and adventure in the heart of Florida. Nestled just 29 kilometers from the attractions of Kissimmee… More

From US$ 694 Book Now

Orangebaum Condo: 8 Min To Disney + Resort Perks

2301 Butterfly Palm Way #305, Kissimmee, United States View map

Situated in the vibrant Kissimmee area, the Orangebaum Condo: 8 Min To Disney + Resort Perks provides an idyllic retreat for families and travelers eager to experience the magic of Disney. Just a… More

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Elite Homes - Eagle Pointe

Eagle Point North And Poinciana Boulevard (Central Location Only; Not Check-In Location), Kissimmee, United States View map

In the tranquil surroundings of Kissimmee, Elite Homes - Eagle Pointe offers guests a serene retreat just 20 minutes from the vibrant attractions of the city. This exquisite selection of vacation… More

From US$ 189 Book Now

Upstay Bella Vida Retreat W Pool Cinema And Games

307 Marcello Boulevard, Kissimmee, United States View map

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Thematic House With Private Pool In A Resort

1136 Challenge Drive, Kissimmee, United States View map

**Welcome to the Thematic House With Private Pool In A Resort**, a captivating retreat that promises an unforgettable getaway in the heart of Kissimmee. Nestled just a 50-minute drive from the… More

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New Listing - Modern Decoration 4 Bedroom Townhouse

4456 Summer Flowers Pl, Kissimmee, United States View map

**Welcome to New Listing - Modern Decoration 4 Bedroom Townhouse Kissimmee, where contemporary design meets unparalleled comfort.** Situated just 7 km from the vibrant heart of Kissimmee, this… More

From US$ 204 Book Now

Villas North Sunshine

1108 Sunset View Circle,, Kissimmee, United States View map

**Experience Unmatched Serenity at Villas North Sunshine** Location is key at Villas North Sunshine, conveniently situated near popular attractions, shopping districts, and the breathtaking scenery… More

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3 Bed 2,5 Bath Perfect Family Home Bunk Beds Townhouse

3006 White Orchid Road, Kissimmee, United States View map

**Welcome to the 3 Bed 2.5 Bath Perfect Family Home Bunk Beds Townhouse**, a delightful retreat located just 32 km from the vibrant city of Kissimmee. This charming townhouse provides an ideal base… More

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Super Luxe- Sleeps 17 - Designs & Near Disney

4444 Summer Flowers Place, Kissimmee, United States View map

Situated in the heart of Kissimmee, the Super Luxe - Sleeps 17 - Designs & Near Disney offers an unparalleled experience for families and large groups seeking adventure and relaxation. Just 7 km from… More

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Windsor At Westside #230868 Home

2167 Tripoli Court, Kissimmee, United States View map

Welcome to Windsor At Westside #230868 Home, an exquisite retreat set in Kissimmee, ideal for families and travelers seeking a blend of luxury and comfort. Nestled just 18 kilometers from the… More

From US$ 445 Book Now

3 Bedrooms 3 Bathrooms Windsor Palms 2340 Sp

2340 Silver Palm Drive, Kissimmee, United States View map

3 Bedrooms 3 Bathrooms Windsor Palms 2340 Sp Kissimmee villa is located 3 km from the A World of Orchids and provides a private pool, ensuring a relaxing stay. More

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2614 Veranda Palms

2614 Tranquility Way, Kissimmee, United States View map

Offering a location around a 25-minute walk from Osceola County, 2614 Veranda Palms Kissimmee villa gives access to various tourist spots in the area. More

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8908 Cc - 6Br Luxury Home: Private Pool

8908 Cabot Cliffs Dr, Kissimmee, United States View map

Set in the vibrant heart of Kissimmee, the 8908 CC - 6Br Luxury Home: Private Pool provides an exquisite escape for families and groups seeking an unforgettable Florida vacation. This opulent six… More

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Unit 9108- Tuscana Resort

1301 Tuscan Terrace Unit 9108, Kissimmee, United States View map

**Welcome to the Tuscana Resort Kissimmee, where comfort meets convenience in the heart of Central Florida.** Just 25 kilometers from the vibrant city of Kissimmee, this inviting retreat is perfect… More

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Private Pool Home At Windsor Palms Resort

8128 Fan Palm Way, Kissimmee, United States View map

Situated in the enchanting Windsor Palms Resort, the Private Pool Home at Windsor Palms Resort offers an idyllic escape just 30 km from Kissimmee's vibrant attractions. This charming residence… More

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Mor2109

2109 Morocco Way, Kissimmee, United States View map

Located 4.5 km from the West Gate Flea Market, Mor2109 Villa Kissimmee gives access to various tourist sites in the vicinity. More

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Disney Getaway Private Pool Themed Bedrooms. Book Now Dw36

2470 Santorini Dr, Kissimmee, United States View map

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