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2026-06-08
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Vacation Rentals in Kissimmee

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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2 Bedroom Modern Apt Near Disney Sl4741

4741 Clock Tower Dr, Apt 303, Kissimmee, United States View map

Discover a delightful retreat at the 2 Bedroom Modern Apt Near Disney Sl4741, ideally nestled in the vibrant area of Kissimmee. This enticing apartment offers a seamless blend of comfort and modern… More

From US$ 145 Book Now

Cozy Apartment Near Disney With 3 Bedrooms 58

2818 Club Cortile Cir, Kissimmee, United States View map

The spacious Cozy Apartment Near Disney With 3 Bedrooms 58 Kissimmee is located 3.5 km from the open-air mall "Lake Buena Vista Factory Stores" and 15 minutes by car from Fun Spot America Kissimmee. More

From US$ 315 Book Now

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

3 Bd 3 Ba Windsor Palms 2357 Sp

2357 Silver Palm Drive, Kissimmee, United States View map

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From US$ 245 Book Now

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

8046 Surf St, Kissimmee, 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$ 321 Book Now

Bikini Bay Cottage With Private Pool Near Disney And Margaritaville Resort & Island H20 Waterpark Access - 3094Ph

3094 Parrot Head Place, Kissimmee, United States View map

Situated about a 10-minute drive from the Pandora, the 8-bedroom Bikini Bay Cottage With Private Pool Near Disney And Margaritaville Resort & Island H20 Waterpark Access - 3094Ph Kissimmee boasts a… More

From US$ 809 Book Now

3161-205Rf Storey Lake, Condo 2/2 Lake View

3161 Paradox Cir #205, Kissimmee, United States View map

Welcome to the tranquil retreat of 3161-205Rf Storey Lake, a stunning condo offering an unparalleled experience for guests seeking both relaxation and adventure. Nestled just 12 kilometers from the… 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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No Stairs 2Br Apartment At Champions Gate Cg781

781 Ocean Course Ave, Kissimmee, United States View map

**Discover the Comfort of No Stairs at Champions Gate** Nestled within the stunning Champions Gate community, No Stairs 2Br Apartment At Champions Gate Cg781 offers a tranquil retreat just 28… More

From US$ 113 Book Now

Unforgettable Escape Fun And Relaxation

Sunshine Ridge Loop 9013, Kissimmee, United States View map

Situated just 32 km from the vibrant city of Kissimmee, the Unforgettable Escape Fun And Relaxation Villa offers an ideal retreat for those seeking a harmonious blend of comfort and adventure. This… More

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Stylish 4Br Townhome Private Pool Bbq & Near Disney

4556 Baleno Lane, Kissimmee, United States View map

Stylish 4Br Townhome Private Pool Bbq & Near Disney Kissimmee villa is situated within a 700-metre distance of the Give Kids The World Village and offers a fitness studio for guests to stay fit. More

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5Br 3Bath Private Townhome 13Min Disney 1496Ft

2316 Caravelle Cir, Kissimmee, United States View map

**Experience the Magic of Orlando from Your Townhome Retreat** Nestled conveniently in Kissimmee, the 5Br 3Bath Private Townhome 13Min Disney offers an ideal getaway for families and groups looking… More

From US$ 240 Book Now

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

8867-103Fu Champions Gate Condo 3 Beds & 2 Baths With Game Room

8867 Cabot Cliffs Dr Unit 103, Kissimmee, United States View map

The spacious 8867-103Fu Champions Gate Condo 3 Beds & 2 Baths With Game Room Kissimmee is located 4.5 km from the Rum Run and 10 minutes' drive from Highlands Reserve GC. Also, there is an outdoor… 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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2776Lo Villa 5 Beds & 5 Baths With Private Pool-Spa

2776 Bookmark Dr, Kissimmee, United States View map

2776Lo Villa 5 Beds & 5 Baths With Private Pool-Spa Kissimmee is located about 5 km from local amusement parks and provides billiards for active guests. 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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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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8102 Vacation Getaway At Windsor

8102 Princess Palm Lane, Apt 205, Kissimmee, United States View map

The spacious 8102-Ibrahim - 8102 Vacation Getaway At Windsor Apartment Kissimmee is 15 minutes' drive from the 145 - foot Tree of Life Sculpture in the Windsor Palms district and welcomes guests with… More

From US$ 89 Book Now

Fantastic 5 Bd Pool Near Disney Resort Perks

2678 Calistoga Ave, Kissimmee, United States View map

Offering a location 4.6 km from Gatorland, the 5-bedroom Fantastic 5 Bd Pool Near Disney Resort Perks Kissimmee villa gives access to various tourist spots in the area. 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

Space For All! 5 Bed In Windsor Island Pool Home!

1890 Summer Drive, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Space For All! 5 Bed In Windsor Island Pool Home! Kissimmee is located 25 minutes' walk from the Rum Run. More

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Spacious Villa W Pool & Game Room

9037 Rhodes Street, Kissimmee, United States View map

Offering a location 25 minutes' stroll from Northeast Regional City Park, Spacious Villa W Pool & Game Room Kissimmee gives access to various tourist spots in the area. Offering a car park as well as… More

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4 Bedrooms Pool Home On Golf Course Fairways Estates

132 Jaybee Ave, Kissimmee, United States View map

**Welcome to 4 Bedrooms Pool Home On Golf Course Fairways Estates**-a luxurious retreat nestled in the serene landscape of Kissimmee, just 35 km from the vibrant heart of the city. This stunning… More

From US$ 199 Book Now

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

Luxury 9 Bd 5 Bath With Private Pool Spa 157

8914 Cabot Cliffs Drive, Kissimmee, United States View map

**Welcome to Luxury 157**, an extraordinary retreat that seamlessly blends comfort and elegance, located in the heart of Kissimmee, just 29 km from the enchanting attractions of the area. With a… More

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Villas At Island Club Community, Pools, Jacuzzi And More!

3135 Britannia Blvd Unit C, Kissimmee, United States View map

To enjoy your vacation in Kissimmee, stay at the 2-room Villas At Island Club Community, Pools, Jacuzzi And More! Kissimmee apartment, which is nearly a 25-minute walk from the Emerald Island… More

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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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Sunset View, Stunning Golf Views Close To Disney, Luxury Condo Near Disney, 045

1110 Sunset View Circle (Building O) Unit #304, Kissimmee, United States View map

Sunset View, Stunning Golf Views Close To Disney, Luxury Condo Near Disney, 045 Kissimmee is located 3.5 km from Mystic Dunes Golf Club and around a 25-minute walk from Orlando Tree Trek Adventure… 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

Cozy Home With Private Pool At Encantada Resort

8580 Bay Lilly Loop, Kissimmee, United States View map

This charming oasis harmoniously blends comfort and convenience, making it an ideal escape for families and couples alike. With Orlando International Airport located a mere 45 kilometers away, your… More

From US$ 129 Book Now

Sweet Suite Sleeps 6 Storey Lake By Shine Villas Apts

3171 Paradox Circle Unit 202 # 903, Kissimmee, United States View map

Welcome to the enchanting Sweet Suite Sleeps 6 Storey Lake By Shine Villas Apts, a perfect retreat for families and friends seeking comfort and relaxation. Nestled just 20 minutes from the vibrant… More

From US$ 126 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

5005 Laguna Bay Cir 18

5005 Laguna Bay Cir #18, Kissimmee, United States View map

Nestled nearly 25 minutes' walk from the miniature Congo River Golf, the 99 m² 5005 Laguna Bay Cir 18 Kissimmee apartment allows guests to explore numerous tourist destinations in the vicinity. The… More

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Edwin Island - Luxury Home, Excellent Location, Gated-Community

2626 Emerald Island Boulevard, Kissimmee, United States View map

Positioned in the heart of Kissimmee, the Edwin Island - Luxury Home, Excellent Location, Gated-Community offers an unparalleled escape for discerning travelers. This exquisite property serves as a… More

From US$ 252 Book Now

Serene Getaway Near Disney

1310 Seasons Boulevard, Kissimmee, United States View map

Welcome to the Serene Getaway Near Disney, an exquisite retreat nestled in the heart of Kissimmee, just 8 km from the enchanting realms of Disney. This idyllic location fosters a perfect blend of… More

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Red Brick House

1045 Partin Drive, Kissimmee, United States View map

Situated approximately a 25-minute walk from Osceola Center for the Arts, Red Brick House Apartment Kissimmee also boasts easy access to Kissimmee train station which is 4.5 km away. Wi-Fi and… More

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Zen Escape At Terra Verde By Shine Villas

4748 Ormond Beach Way, Kissimmee, United States View map

To enjoy your vacation in Kissimmee, stay at the 3-room Zen Escape At Terra Verde By Shine Villas Kissimmee apartment, which is nearly a 25-minute walk from the Osceola County Welcome Center and… More

From US$ 146 Book Now

Near Disney Parks! Nice Home!

50989 U.S. 27 #375, Kissimmee, United States View map

**Discover the Enchantment of Near Disney Parks! Nice Home!** Nestled just 35 km from the magical escapades of Disney Parks, Near Disney Parks! More

From US$ 179 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

Poolside Oasis In Paradise Palms: 6 Mi To Disney!

8976 California Palm Rd, Kissimmee, United States View map

Located in the West Kissimmee district of Kissimmee and approximately a 5-minute walk from the Paradise Palms Boulevard, Poolside Oasis In Paradise Palms: 6 Mi To Disney! Kissimmee villa provides… More

From US$ 231 Book Now

Strategic Condo 2 Bd Close To Disney Storey Lake

Paradox Circle 3150, Kissimmee, United States View map

**Welcome to Strategic Condo 2 Bd Close To Disney Storey Lake** Nestled in the vibrant locale of Kissimmee, the Strategic Condo 2 Bd Close To Disney Storey Lake promises an exceptional blend of… More

From US$ 122 Book Now