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2026-04-22
2026-04-23
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Kissimmee holiday rentals

Tropical Style Ground Floor Unit In Bahama Bay

302 Rum Run, Kissimmee, United States View map

Welcome to the Tropical Style Ground Floor Unit in Bahama Bay, an exquisite retreat nestled in Kissimmee, just 33 km from the vibrant town. This charming villa perfectly encapsulates the essence of… More

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Shvpc3 - Paradise Cay #3 - 3 Bed 25 Baths Townhome

5273 Paradise Cay Cir, Kissimmee, United States View map

During the stay at Shvpc3 - Paradise Cay #3 - 3 Bed 25 Baths Townhome Kissimmee villa, guests can indulge in a hot tub or visit local amusement parks, located 2.6 km away. More

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Last Minute Disney Getaway Private Pool Themed Bedrooms. Book Now 56757

4218 Paragraph Drive, Kissimmee, United States View map

The 3-bedroom Last Minute Disney Getaway Private Pool Themed Bedrooms. Book Now 56757 Kissimmee villa is located within 7 km of Old Town Shopping Mall and provides a treatment room. This Kissimmee… More

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6Br Villa W Private Pool At Champions Gate

9127 Sommerset Hills Dr, Kissimmee, United States View map

Situated 2.6 km from ChampionsGate Golf Club, 6Br Villa W Private Pool At Champions Gate Kissimmee provides access to numerous tourist attractions in the area. More

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8911 Tropical Haven Court

8911 Tropical Haven Court, Kissimmee, United States View map

Set in the serene surroundings of Kissimmee, the 8911 Tropical Haven Court Villa offers an exquisite retreat for families and friends seeking an unforgettable getaway. Just a short 32 kilometers from… More

From US$ 648 Book Now

4 Bedroom 3 Bathroom Villas At Sevendwarfs 31-107

2601 Gala Road South 31-107, Kissimmee Fl, 34746, Kissimmee, United States View map

Welcome to the enchanting **4 Bedroom 3 Bathroom Villas at Sevendwarfs 31-107**, located just a scenic 20-minute drive from the vibrant heart of Kissimmee. This charming retreat offers a perfect… More

From US$ 204 Book Now

Fourth Floor Penthouse With Shared Pools And Hot Tub, Fast Wifi, & Central Ac

4721 Clock Tower Drive, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Fourth Floor Penthouse With Shared Pools And Hot Tub, Fast Wifi, & Central Ac Kissimmee villa is located 6 km from the World of Disney. More

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4 Bedrooms 3 Bathrooms Storey Lake 4931 Wa

4931 Windermere Avenue, Kissimmee, United States View map

Nestled in the idyllic surroundings of Kissimmee, 4 Bedrooms - 3 Bathrooms - Storey Lake 4931 Wa beckons travelers seeking an enchanting retreat. This stylish abode harmoniously imbues comfort and… More

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Family Getaway Near Disney Parks

2903 Edenshire Way, Kissimmee, United States View map

Family Getaway Near Disney Parks Kissimmee villa is located nearly a 10-minute ride from the Congo River Golf and provides guests with a hot tub for a more relaxing stay. More

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La Isla At Paradise By Propertychekker!

8661 La Isla Drive, Kissimmee, United States View map

Situated in the West Kissimmee district of Kissimmee, 4.7 km from the Pandora, La Isla At Paradise By Propertychekker! Kissimmee villa comes with a private swimming pool for guests to unwind. This… More

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Orlando Villa 6441: Spacious 6Br Pool Home Near Disney

346 Riggs Circle, Kissimmee, United States View map

Welcome to Orlando Villa 6441, a stunning six-bedroom pool home located just a short drive from the enchanting Disney theme parks. Nestled in Kissimmee, this spacious haven combines luxury with… More

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True Fantasies 101

4013 Venetian Bay Drive 101, Kissimmee, United States View map

Situated 2.5 km from the working Kissimmee Air Museum, True Fantasies 101 Kissimmee villa invites guests to relax at a sunbathing terrace. Guests can enjoy hiking, cycling, and pool at the property… More

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Centre Court Seagrove

1356 Centre Court Ridge Drive, Kissimmee, United States View map

**Experience Elegance and Comfort at Centre Court Seagrove** Conveniently located near major attractions, Centre Court Seagrove provides easy access to popular destinations, including theme parks… More

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Ruby-Rose Retreat By Paradise Resort Vacations

1204 Winding Hollow Court, Kissimmee, United States View map

Situated 3.1 km from Oren Brown Community Park, Ruby-Rose Retreat By Paradise Resort Vacations Kissimmee villa features a patio with views of the lake. Offering a swimming pool, this accommodation… More

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6Br In Reunion Resort Sleeps 14 And 12 Min Disney

7692 Somersworth Drive, Kissimmee, United States View map

Situated 15 minutes by car from the Reunion Resort Water Park, 6Br In Reunion Resort Sleeps 14 And 12 Min Disney Kissimmee villa invites guests to relax at a terrace. More

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Themed Resort Villa With Pool Spa

4798 Kings Castle Circle, Kissimmee, United States View map

Located nearly 20 minutes' walk from the Marshalls|the Marshalls store, the 5-bedroom Themed Resort Villa With Pool Spa Kissimmee features a private pool with a pool cover. Featuring access to a… More

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Monthly Discounts Private Pool 944

944 Emerald Green Court, Kissimmee, United States View map

Offering a location 3.9 km from the Dare 2 Escape escape room, Monthly Discounts Private Pool 944 Villa Kissimmee gives access to various tourist spots in the area. More

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Resort Condo With Pools, Hot Tub, Game Room, Tennis, Gym, Balcony, Ac, & W/D

2302 Butterfly Palm Way, Kissimmee, United States View map

Located 4.8 km from the Reunion Resort Water Park, Resort Condo With Pools, Hot Tub, Game Room, Tennis, Gym, Balcony, Ac, & W/D Kissimmee villa gives access to various tourist sites in the vicinity. More

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5 Bedrooms4.5 Bathroomswindsor Westside 2402Td

2402 Tangier Dr, Kissimmee, United States View map

Featuring a private swimming pool for guests' relaxation, the 4-bedroom 5 Bedrooms 45 Bathrooms Windsor At Westside 2402 Td Kissimmee villa is located nearly a 10-minute ride from Highlands Reserve… More

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Homestead Hideaway

1205 Molona Street, Kissimmee, United States View map

Nestled in the enchanting Kissimmee region, the Homestead Hideaway offers an inviting retreat just 22 km from the bustling heart of Kissimmee. This delightful destination combines the charm of homely… More

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Fabulous Cottage With Private Pool Near Disney With Margaritaville Resort & Island H2O Access - 8094Kd

Knee Deep Road, Orlando, United States View map

The 3-bedroom Fabulous Cottage With Private Pool Near Disney With Margaritaville Resort & Island H2O Access - 8094Kd Kissimmee offers proximity to nearby tourist spots, such as the Avatar Flight of… More

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Lake View Condo With Resort

3151 Paradox Circle 302, Kissimmee, United States View map

Situated 4.8 km from Fun 'n Wheels Family Fun Park|the Fun 'n Wheels Family Fun Parks, Lake View Condo With Resort Kissimmee villa entices guests to explore various tourist attractions in the area. More

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Spacious Orlando Stay Near Disney

4362 Phrase Street, Kissimmee, United States View map

Staying at Spacious Orlando Stay Near Disney Kissimmee villa, guests can easily reach the Falcon's Fire Golf Course, located approximately 6 km away. More

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Mvp 1511Abib Long Term

1511 Antigua Bay Drive, Kissimmee, United States View map

Set just 13 kilometers from the vibrant heart of Kissimmee, the Mvp 1511Abib Long Term Villa offers a serene retreat infused with comfort and style. This charming villa serves as a perfect base for… More

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Fairway North Shore

737 Desert Mountain Dr, Kissimmee, United States View map

Set just 27 kilometers from the vibrant heart of Kissimmee, Fairway North Shore invites guests to experience a blend of comfort and luxury in a premier setting. This exquisite retreat offers a… More

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5 Bedrooms 4 Bathrooms Storey Lake 4198 Pd

4198 Paragraph Drive, Kissimmee, United States View map

**Welcome to Storey Lake 4198 Pd** Nestled in the heart of Kissimmee, Storey Lake 4198 Pd is your gateway to a remarkable retreat just 10 km from the bustling main attractions of Kissimmee and a… More

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Classical 3 Bdrm Condo With Private Ground Floor Patio At Reunion

7658 Whisper Way M104, Kissimmee, United States View map

Nestled in the heart of Kissimmee, the Classical 3 Bedroom Condo with Private Ground Floor Patio at Reunion offers a perfect retreat for travelers seeking comfort and convenience. This beautifully… More

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1094Ssp-The Retreat At Championsgate Home

1094 Splash Shot Place, Kissimmee, United States View map

Situated in the heart of ChampionsGate, 1094Ssp-The Retreat At Championsgate Home is a tranquil oasis just a 50-minute drive from the vibrant attractions of Kissimmee. This luxurious retreat combines… More

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Casa 4Q C/ Piscina + Quartos Mickey E Star Wars

954 Splash Shot Place, Kissimmee, United States View map

Casa 4Q C/ Piscina + Quartos Mickey E Star Wars Kissimmee is located around 10 minutes by car from the Rum Run and provides an indoor pool. More

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4Br Themed Home W Resort Pool Near Disney

5370 Diplomat Court #104, Kissimmee, United States View map

Welcome to 4Br Themed Home W Resort Pool Near Disney, a vibrant family retreat located just 20 minutes from the enchanting attractions of Kissimmee. This charming abode offers an immersive experience… More

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Family 6Br Home, Pool, Game Room And Themed Rooms

8987 Amelia Downs Trail, Kissimmee, Fl 34747, Usa, Kissimmee, United States View map

Situated 2.5 km from Highlands Reserve GC, Family 6Br Home, Pool, Game Room And Themed Rooms Kissimmee entices guests to explore various tourist attractions in the area. More

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Radiant 4 Bdrm Retreat With Golf Course Views At Reunion

1129 Castle Pines Ct., Kissimmee, United States View map

**Welcome to Radiant 4 Bedroom Retreat with Golf Course Views at Reunion**, a luxurious getaway nestled in the heart of Kissimmee. More

From US$ 395 Book Now

Stunning Emerald Island Resort Vacation Home With Pool Spa And Access To Clubhouse

8593 La Isla Drive, Kissimmee, United States View map

Offering a hot tub for a relaxing experience, Stunning Emerald Island Resort Vacation Home With Pool Spa And Access To Clubhouse Kissimmee is located a 15-minute drive from the Dinosaur attraction. More

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Villa Rios Camilo - Lucaya Village

5362 Diplomat Ct  Building 18 -  Unit 107, Kissimmee, United States View map

Situated 2.5 km from the Gaylord Palms Resort & Convention Center, Villa Rios Camilo - Lucaya Village Kissimmee provides access to numerous tourist attractions in the area. More

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Cozy Home Storey Lake Resort Pool Spa Near Disney

2736 Bookmark Dr, Kissimmee, United States View map

Located just 650 metres from Fun Spot America Kissimmee, the 5-bedroom Cozy Home Storey Lake Resort Pool Spa Near Disney Kissimmee boasts an outdoor swimming pool, a Jacuzzi for a relaxing experience… More

From US$ 443 Book Now

Windsor Palms Home - Pool, Theatre &Near Disney

8105 Coconut Palm Way Unit 205, Kissimmee, United States View map

Welcome to the Windsor Palms, a charming resort nestled in the heart of Kissimmee, just a stone's throw from the enchanting Disney parks. This inviting retreat showcases a blend of modern amenities… More

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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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2744Hm Villa 5 Bed/5 Ba

2744 Bookmark Dr, Kissimmee, United States View map

Osceola County is Florida. This exquisite villa offers a sanctuary of comfort and modern amenities, ensuring a memorable getaway for families or groups. More

From US$ 199 Book Now

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

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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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