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2026-04-23
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Kissimmee holiday rentals

Luxury 7 Bedroom 5 Bath Pool Home 210

761 Sticks Street, Kissimmee, United States View map

In a serene enclave just 29 km from the bustling heart of Kissimmee and only 50 km from Orlando International Airport, the Luxury 7 Bedroom 5 Bath Pool Home 210 offers an idyllic retreat for families… More

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Once Upon A Stay

4908 Coral Castle Dr, Kissimmee, United States View map

**Discover the Charm of Once Upon A Stay Kissimmee** Once Upon A Stay Kissimmee effortlessly combines the enchantment of fairy-tale living with contemporary comforts, making it a perfect destination… More

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Heavenly Hideaway Windsor At Westside Ww104

2159 Tripoli Ct, Kissimmee, United States View map

Welcome to the Heavenly Hideaway, a serene retreat nestled within the picturesque Windsor At Westside, just a short drive from the enchanting streets of Kissimmee. Immerse yourself in the tranquility… More

From US$ 720 Book Now

Spacious 8Br Family Villa With Pool, Game Room & Bbq, Kissimmee, Near Disney!

1941 Nice Court, Kissimmee, United States View map

Situated around a 10-minute ride from Northeast Regional City Park, Spacious 8Br Family Villa With Pool, Game Room & Bbq, Kissimmee, Near Disney! features a terrace with views of the garden. Offering… More

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7 Mi To Disney Davenport Townhome With Patio And Pool

8131 Roseville Blvd, Kissimmee, United States View map

Situated about 10 minutes by car from Orlando Tree Trek Adventure Park|the Orlando Tree Trek Adventure Park, the 3-bedroom 7 Mi To Disney Davenport Townhome With Patio And Pool Kissimmee villa… More

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Epic Encanto Home With Free Water Park Disney10 Miles

4373 Quote Street, Kissimmee, United States View map

**Welcome to Epic Encanto Home With Free Water Park, a delightful retreat situated just 10 miles from the enchanting world of Disney.** Located in the heart of Kissimmee, this family-friendly… More

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Cute Condo In Bahama Bay With Big Balcony

107 New Providence Promenade, Kissimmee, United States View map

Welcome to the enchanting Cute Condo In Bahama Bay With Big Balcony, a serene retreat nestled just 33 km from the vibrant heart of Kissimmee. Perfectly situated to explore the wonders of Central… More

From US$ 133 Book Now

Dluxx Top Dream House Pool At Windsor Resort 1704

1704 Lima Avenue, Kissimmee, United States View map

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Luxury 6 Bedroom 5 Bath Pool Home 201

680 Sticks Street, Kissimmee, United States View map

Nestled in the serene surroundings of Kissimmee, the Luxury 6 Bedroom 5 Bath Pool Home 201 invites guests into an oasis of relaxation and comfort. With a mere 50-minute drive from the vibrant city of… More

From US$ 585 Book Now

Spacious Home With Private Pool Near Disney With Waterpark & Resort Access At Encore Resort - 7720Ff

7720 Fairfax Drive, Kissimmee, United States View map

**Welcome to Encore Resort - 7720Ff, your idyllic retreat just moments away from the magic of Disney.** Nestled in the charming town of Celebration, a creation of The Walt Disney Company, this… More

From US$ 696 Book Now

Esmerald Island Resort Oasis: Your Perfect Getaway Near Disney

8460 Crystal Cove Loop Kissimmee, Fm 34747, Kissimmee, United States View map

**Welcome to Esmerald Island Resort Oasis: Your Perfect Getaway Near Disney** Nestled just a short scenic drive from the enchanting attractions of Kissimmee, Esmerald Island Resort Oasis offers an… More

From US$ 160 Book Now

Best Vacation Villa, Themed Beds, Private Pool

Windermere Avenue 5001, Kissimmee, United States View map

**Experience a Dream Getaway at Best Vacation Villa in Kissimmee** Conveniently located only 30 kilometers from Orlando International Airport, the Best Vacation Villa offers easy access for travelers… More

From US$ 269 Book Now

Family & Group Haven-Resort Style Living-Near Disney

126 Pompano Beach Drive, Kissimmee, United States View map

Located nearly a 10-minute ride from Kissimmee Golf Club, the 3-bedroom Family & Group Haven-Resort Style Living-Near Disney Kissimmee villa offers a patio with views of the lake. Offering a swimming… More

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Stunning Home At Storey Lake Close To Disney

2972 Protagonist Street, Kissimmee, United States View map

Stunning Home At Storey Lake Close To Disney is where comfort and whimsical adventure beautifully intertwine. Nestled just 10 km from the vibrant heart of Kissimmee, this captivating venue provides… More

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Rare!Lake Front Pool-Spa, Close To Clubhouse-1691C

4745 Kings Castle Circle, Kissimmee, United States View map

Located 4.6 km from the Old Town, Rare!Lake Front Pool-Spa, Close To Clubhouse-1691C Kissimmee villa entices guests to relax in a hot tub. More

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4983Bs - Bawtry Estate

Kissimmee, United States View map

**Welcome to 4983Bs - Bawtry Estate, a serene retreat nestled just 15 kilometers from the vibrant heart of Kissimmee.** This luxurious villa embodies the perfect blend of elegance and comfort… More

From US$ 218 Book Now

Lazy River Game Room & Heated Pool 10Mi To Disney

9052 Sommerset Hills Drive, Kissimmee, United States View map

Situated 4.2 km from Highlands Reserve GC, Lazy River Game Room & Heated Pool 10Mi To Disney Kissimmee villa entices guests to explore various tourist attractions in the area. More

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Sunkissed Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8046Su

8046 Surf St, Orlando, United States View map

The 3-bedroom Sunkissed Cottage With Hot Tub Near Disney With Margaritaville Resort & Island H2O Access - 8046Su Kissimmee is located around 10 minutes' drive from The Legends Golf Course, giving… More

From US$ 366 Book Now

Stylish Home At Amazing Resort! Sla103

2162 Fleming Mist Place, Kissimmee, United States View map

Featuring a private swimming pool for guests' relaxation, the 4-bedroom Stylish Home At Amazing Resort! Sla103 Kissimmee is located about a 25-minute stroll from Highlands Reserve GC. More

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Level Up Your Vacation Stylish Home Near Disney

5236 Paradise Cay Circle, Kissimmee, United States View map

Situated 20 minutes' walk from the open-air mall "Lake Buena Vista Factory Stores", Level Up Your Vacation Stylish Home Near Disney Kissimmee invites guests to relax at a patio. More

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Chic Retreat - Unforgettable Stay

Penelope Loop 2959, Kissimmee, United States View map

**Chic Retreat - Unforgettable Stay Kissimmee** offers a serene escape just 10 kilometers from Kissimmee and 40 kilometers from Orlando International Airport. Nestled in a picturesque setting, this… More

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Beautiful 4 Bedroom 3 Bath Pool Townhome 280

4287 Paragraph Dr, Kissimmee, United States View map

**Welcome to the Beautiful 4 Bedroom 3 Bath Pool Townhome 280**, a serene retreat just 10 km from the vibrant heart of Kissimmee. Nestled in a peaceful community, this exquisite accommodation blends… More

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Paradise 4Bd W Private Pool & Waterpark 8951

2941 Banana Palm Drive, Kissimmee, United States View map

Located about 6 km from the Tree of Life, Paradise 4Bd W Private Pool & Waterpark 8951 Kissimmee villa offers cycling, as well as a fitness club for active guests. Featuring a patio, this property is… More

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Great Townhouse In Gated Community West Lucaya

3211 Wish Avenue, Kissimmee, United States View map

Welcome to the Great Townhouse in Gated Community West Lucaya, an exquisite villa that offers an elegant retreat in the heart of Florida's vibrant Kissimmee. Nestled within a secure and serene… More

From US$ 193 Book Now

4321 Qs - Magical Haven Townhome W Pool

4321 Quote Street, Kissimmee, United States View map

Welcome to the enchanting 4321 Qs - Magical Haven Townhome W Pool, a tranquil getaway located just a 20-minute drive from the heart of Kissimmee. Nestled within the vibrant surroundings of Central… More

From US$ 105 Book Now

2776Lo Villa 5 Bed/5 Ba

2776 Bookmark Dr, Kissimmee, United States View map

2776Lo Villa is a luxurious retreat nestled in the heart of Kissimmee, just 20 minutes by car from Orlando's enchanting theme parks. This stunning vacation home combines comfort and sophistication… More

From US$ 218 Book Now

2820 Rocella Court

2820 Rocella Court, Kissimmee, United States View map

Set in the enchanting surroundings of Kissimmee, the 2820 Cozy Gem In Kissimmee With Pool offers a sanctuary of comfort and relaxation just 33 km from the vibrant attractions of Kissimmee and 50 km… More

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Beautiful Royal Palm Bay Condo Near Disney

2014 Royal Bay Boulevard, Kissimmee, United States View map

Set in the enchanting landscape of Kissimmee, the Beautiful Royal Palm Bay Condo Near Disney is a delightful retreat for families and adventure seekers alike. This inviting destination places guests… More

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Relaxing 3Br Haven For 8 At Seven Dwarfs Sd2610

2610 Lodi Circle, Unit #105 - Building 1, Kissimmee, United States View map

**Welcome to Relaxing 3Br Haven For 8 At Seven Dwarfs Sd2610**-a serene retreat in Kissimmee that perfectly balances comfort and convenience. Nestled just a 10-minute drive from the bustling heart of… More

From US$ 179 Book Now

Upstay Home W Pool Hot Tub & Patio - Pet Friendly

5445 Dahlia Reserve Drive, Kissimmee, United States View map

**Welcome to Your Oasis in Kissimmee** The prime location provides easy access to the attractions of Kissimmee and beyond, making Upstay Home W Pool Hot Tub & Patio - Pet Friendly a convenient base… More

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2040Ma Villa 7 Bed/6.5 Ba

2040 Fleming Mist Ln, Kissimmee, United States View map

Positioned in the enchanting region near Kissimmee, the 2040Ma is a luxurious villa that redefines comfort with its impressive array of amenities. Just 32 km from the vibrant attractions of Kissimmee… More

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Haven Beautiful 3 Bedroom Th In Gated Resort Community

4000 San Gallo Dr, Kissimmee, United States View map

Welcome to Haven, a charming retreat nestled in a secure gated resort community, just 6 km from the vibrant city of Kissimmee. This exquisite property provides an idyllic oasis for families and… More

From US$ 126 Book Now

Five-Bedroom House

1890 Summer Drive, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Five-Bedroom House Kissimmee villa is located 25 minutes' walk from the Rum Run. More

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Bsv_Villa8912

8912 Bengal Ct, Kissimmee, United States View map

The 10-room Bsv_Villa8912 Kissimmee villa is located 2.9 km from the Rum Run and boasts a swimming pool provided on a terrace for a pleasant stay. Nestled in the West Kissimmee district of Kissimmee,… More

From US$ 619 Book Now

600 Pebble Beach Drive

600 Pebble Beach Drive, Kissimmee, United States View map

**Welcome to 600 Pebble Beach Drive**, an exquisite retreat nestled in the enchanting Kissimmee region, just 29 kilometers from the heart of Kissimmee and conveniently located 50 kilometers from the… More

From US$ 202 Book Now

53 Private Pool House Near All Famous Attractions!!!

729 Downing Cir, Kissimmee, United States View map

Offering a location around a 25-minute walk from Highlands Reserve GC, the 3-bedroom 53 Private Pool House Near All Famous Attractions!!! Kissimmee villa gives access to various tourist spots in the… More

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Casa 4Q | Piscina Privativa | 10 Min Da Disney

4815 Dedication St, Kissimmee, United States View map

Situated 4.9 km from the World of Disney, the 3-bedroom Casa 4Q | Piscina Privativa | 10 Min Da Disney Kissimmee provides access to numerous tourist attractions in the area. More

From US$ 206 Book Now

1531 Carey Palm

1531 Carey Palm Circle, Kissimmee, United States View map

Nestled in the vibrant heart of Kissimmee, the 1531 Carey Palm Villa boasts an unparalleled blend of luxury and comfort. This exquisite retreat is conveniently located just 32 km from the captivating… More

From US$ 367 Book Now

Dog-Friendly Townhome Wsplashpool -3201Pp

8930 Majesty Palm Road,, Kissimmee, United States View map

Located in the West Kissimmee district of Kissimmee and 3.3 km from Polo Park Golf Course, the 3-bedroom Dog-Friendly Townhome Wsplashpool -3201Pp Kissimmee villa provides guests with a Jacuzzi and… More

From US$ 309 Book Now

Free Water Park Walking Distance! Chg108

1069 Splash Shot Place, Kissimmee, United States View map

Offering a location 10 minutes by car from the Rum Run, Free Water Park Walking Distance! Chg108 Villa Kissimmee gives access to various tourist spots in the area. More

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2738We Villa 5 Bed/5 Ba

2738 Bookmark Dr, Kissimmee, United States View map

**Welcome to 2738We Villa 5 Bed/5 Ba in Kissimmee, the ultimate home-away-from-home destination.** This exquisite villa redefines comfort and luxury with its expansive living spaces, featuring five… More

From US$ 287 Book Now

Modern 5Br Twnhome W Private Pool Near Disney 358

8894 Geneve Ct, Kissimmee, United States View map

### Welcome to Modern 5Br Twnhome W Private Pool Near Disney 358 Conveniently located, Modern 5Br Twnhome W Private Pool Near Disney 358 offers easy access to major attractions, making it perfect for… More

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Cozy Family 3Br Townhouse Perfect Stay For 6 Guests

904 Park Terrace Circle, Kissimmee, United States View map

Situated just a short 10-minute drive from the vibrant heart of Kissimmee, the Cozy Family 3Br Townhouse Perfect Stay For 6 Guests offers an idyllic retreat for families and groups. With its prime… More

From US$ 239 Book Now

Terra Verde Resort!! Private Pool, Game Room, Near Disney And Universal!!

204 Hideaway Beach Lane, Kissimmee, United States View map

Staying at the 3-bedroom Terra Verde Resort!! Private Pool, Game Room, Near Disney And Universal!! Kissimmee villa, guests can easily reach the Falcon's Fire Golf Course, located around 7 km away. More

From US$ 163 Book Now

Magical 7Br Resort Pool Home Near Disney & Orlando Attractions

4693 Golden Beach Court, Kissimmee, United States View map

**Welcome to the Magical 7Br Resort Pool Home Near Disney & Orlando Attractions**, a perfect retreat blending comfort and convenience for families and groups seeking an unforgettable stay. Located… More

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Magical Kissimmee Retreat With Themed Rooms Pool Near Disney

8952 Adriatico Lane, Kissimmee, United States View map

**Indulge in the Enchantment of Magical Kissimmee Retreat** With its prime location near the enchantment of Disney and other attractions, Magical Retreat serves as a perfect base for exploring the… More

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5 Bedroom 4 Bathroom Windsor At Westside 8933Pw

8933 Prague Way, Kissimmee Fl, 34747, Kissimmee, United States View map

Situated within the enchanting surroundings of Kissimmee, the 5 Bedroom 4 Bathroom Windsor At Westside 8933Pw is a luxurious sanctuary perfect for families or groups looking to experience the magic… More

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1517 Reunion

1517 Fairview Cir, Kissimmee, United States View map

**1517 Reunion Villa is your perfect sanctuary in the heart of Kissimmee's Patriot's Landing.** This charming home boasts stunning front lake views and an inviting rear private pool featuring a… More

From US$ 323 Book Now

Shvpc3 - Paradise Cay #3 - 3 Bed 2.5 Baths Townhome

5273 Paradise Cay Cir, Kissimmee, United States View map

This delightful residence provides a serene retreat while keeping you close to the attractions of Central Florida. The interior is beautifully designed, offering a perfect blend of modern aesthetics… More

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6Br W Heated Pool + 9Mi To Disney + Sleeps 14

210 Ballo Drive, Kissimmee, United States View map

**Welcome to 6Br W Heated Pool + 9Mi To Disney + Sleeps 14, your ultimate family escape close to the magical allure of Disney.** Nestled in the heart of Kissimmee, this inviting residence offers not… More

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