Holiday houses in Kissimmee

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Top-rated holiday rentals in Kissimmee

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Condo in Kissimmee
4.95 out of 5 average rating, 183 reviews

3161-305 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top Guest favourite
A compact kitchen features white cabinetry and modern stainless steel appliances. An electric stovetop is positioned beside a microwave, with a coffee maker and various kitchen utensils visible. A small refrigerator stands nearby, complemented by decorative items on the open shelves.
Home in Kissimmee
4.99 out of 5 average rating, 130 reviews

Private Suite with Independent Entrance

Private Suite with Independent Entrance Kissimmee, Fl Enjoy a modern and fully equipped private suite, perfect for couples or travelers looking for comfort, privacy, and a relaxing stay just minutes away from Orlando’s top attractions. 📍Perfect Location Conveniently located in Kissimmee, just minutes from: 🎢 Disney World 🎬 Universal Studios 🌊 SeaWorld and Aquatica You’ll also find restaurants, supermarkets, outlets, and gas stations nearby an excellent location for your Orlando vacation!

Top Guest favourite
The living area features a spacious gray sectional sofa arranged around a white coffee table, with decorative items adding style. A large window provides natural light, complemented by modern shelving and a lamp. The open kitchen is visible in the background, emphasizing a comfortable layout.
Apartment in Kissimmee
5 out of 5 average rating, 55 reviews

Modern Luxury Kissimmee Retreat

Welcome to our stunning Kissimmee apartment, where modern luxury meets ultimate comfort! This renovated 2-bedroom, 2-bathroom retreat offers high-end finishes, a fully equipped kitchen, large screen TVs, PlayStation 5, and high-speed Wi-Fi. Enjoy blackout curtains and white noise machines for restful nights. Complex amenities include a pool, gym, sauna, and tennis court. Located near Walt Disney World, Universal Studios, and top shopping, our apartment is the perfect base for your adventures.

Guest favourite
A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.
Home in Kissimmee
4.94 out of 5 average rating, 71 reviews

Paradise Suite

Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles

Top Guest favourite
The entrance to the studio is shown, featuring a solid grey door with a simple handle. A small welcome mat is placed at the door. A wooden fence provides privacy, while a small porch area is seen beside the entrance.
Apartment in Kissimmee
4.97 out of 5 average rating, 70 reviews

Small Studio Apartment

The apartment is attatched to the main house, but has its own entrance. The studio will provide guest with complete privacy The kitchen is equipped with a fully furnished setup; including pots, pan oven, fridge and more. Full size bed is provided. Bathroom will have towels, soap, shampoo, conditioner, and hair dryer Othe amenities include a TV with Netflix, wifi, Alexa, window AC unit, parking right in front, and a quiet neighborhood. Any questions or concerns you can contact me.

Top Guest favourite
Apartment in Orlando
4.93 out of 5 average rating, 14 reviews

*NEW* Villa Amalfi Boho• FreeParksShuttle•PoolView

Welcome to Villa Amalfi, a brand-new, boho-inspired luxury retreat located in the heart of Lake Buena Vista – Orlando, just minutes from Disney, Universal, and Orlando’s best shopping and dining. Enjoy free shuttle service to the theme parks, so you can relax and focus on making memories - no parking stress — no extra cost. This thoughtfully designed space blends Mediterranean charm with cozy textures and natural tones. Every corner was curated to offer both comfort and style.

Top Guest favourite
Apartment in Winter Garden
5 out of 5 average rating, 34 reviews

Bliss Vibes King Bed 12 Min-Parks/Shops/Golf

Find your calm at Boho Bliss Haven—a stylish, professionally cleaned escape just 12 minutes from the theme parks. This cozy retreat blends earthy tones and boho charm to create a relaxing, curated space. We've provided everything for your comfort and enjoyment. Dive into the pool, unwind with games, or hit the gym nearby. Our prime location is minutes from theme parks, restaurants, shopping, and golf courses. Boho Bliss Haven offers comfort, convenience, and a touch of magic.

Top Guest favourite
A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.
Home in Kissimmee
4.99 out of 5 average rating, 145 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌴 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Top Guest favourite
A modern digital door lock is mounted on a light-colored door, featuring a keypad for secure access. A blurred plant with lush green leaves is visible in the background, adding a touch of nature to the entryway.
Guest suite in Kissimmee
4.95 out of 5 average rating, 144 reviews

It's too much like a elegant mini-hotel (5)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience.

Top Guest favourite
Guesthouse in Kissimmee
4.98 out of 5 average rating, 281 reviews

"Little Blue House" Getaway Near the Disney Parks

Your home away from home! Enjoy a comfortable and relaxing stay in our Casa Azul. Spacious and modern, it features a bedroom with a double bed, a private bathroom, a living room with a sofa bed, a dining room, and a fully equipped kitchen. Ideal for vacations with family or friends.

Top Guest favourite
A spacious room is divided into a sleeping area with two beds dressed in neutral tones and a cozy seating area with a dark sofa. Natural light enters through a window, and a simple dining table is set with plates and cutlery.
Apartment in Kissimmee
4.98 out of 5 average rating, 187 reviews

Comfortable Apartment in Kissimmee

Welcome to our apartment, a cozy and warm place where you can get away for a vacation or a business trip. My family and I will try our best to make your stay unique and unforgettable. So, please feel at home and make great memories in the city.

Top Guest favourite
A refreshing swimming pool features a large water slide in vibrant green and blue. Palm trees provide shade around the area. Several lounge chairs are positioned beside the pool, inviting relaxation while enjoying the sunny landscape.
Condo in Kissimmee
4.96 out of 5 average rating, 148 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

2 Bedroom condominium 10 minutes away from most attractions with State-of-the-art finishes and a unique personal touch from the Family Who runs it with years of experience hosting in places around the world .

Popular amenities for Kissimmee holiday rentals

When is the best time to visit Kissimmee?

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Avg. price$217 AUD$223 AUD$232 AUD$226 AUD$200 AUD$212 AUD$238 AUD$207 AUD$189 AUD$195 AUD$207 AUD$244 AUD
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Quick stats about holiday rentals in Kissimmee

  • Total holiday rentals

    Explore 7,290 holiday rentals in Kissimmee

  • Verified guest reviews

    Over 257,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    6,160 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,150 rentals that welcome pets

  • Holiday rentals with a pool

    6,590 properties feature pools

  • Rentals with dedicated workspaces

    4,000 properties have a dedicated workspace

  • Wi-Fi availability

    7,110 of Kissimmee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Pet friendly and Laptop-friendly workspace across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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  4. Osceola County
  5. Kissimmee