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Holiday rentals in Kissimmee

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Kissimmee

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

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Guest favourite
A light-filled living area is highlighted by a ceiling fan and a wall-mounted television displaying ESPN+. Two armchairs in a neutral tone and a sleek coffee table are positioned around a comfortable sofa, while large sliding doors open to a spacious balcony.
Flat in Kissimmee
4.95 out of 5 average rating, 75 reviews

Cozy Condo Only 6 Minutes From Disney World

Step into our inviting condo, where coziness embraces you! Our charming property is strategically located only 6 minutes from the Theme Parks, prestigious Outlets, and excellent Restaurants. Experience the comfort of having ample space for up to 5 guests, with a King Size bed in the suite and a Twin-Full Bunk Bed available. Experience luxury living with our high-quality furniture and decor. Our Condo is fully equipped with a modern open-style kitchen and appliances, high-speed WiFi 5G, Cable

Top guest favourite
The cottage features a vibrant blue exterior with yellow accents on the balcony and windows. Tropical landscaping with palm trees frames the entrance, complemented by a covered porch. The structure is two stories high, showcasing a welcoming atmosphere in a gated community.
Home in Kissimmee
4.98 out of 5 average rating, 50 reviews

Margaritaville Cottage,Hot Tub,Arcade, near Disney

Kick back and relax in this cozy two-bedroom cottage inside the gated Margaritaville Resort, only 4 miles from Disney. While the kids have a blast playing over 1,000 games on the full-size arcade machine inside, you can chill out on the patio with a cold drink. Forget crowded resort pools- you’ve got your own private hot tub to unwind in after a long day at the parks. Sunset Walk and the new Island H2O water park are just a short walk away. And bring your furry friend too — we’re pet friendly!

Guest favourite
Villa in Kissimmee
4.82 out of 5 average rating, 38 reviews

Luxury Townhouse Near Disney | 3BR

Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!

Guest favourite
A welcoming living area features a dark brown sofa adorned with decorative pillows in warm tones. Greenery decorates the wall behind the sofa, complemented by a modern lamp. A nearby circular table and chair set add to the inviting space, with natural light filtering through a window.
Flat in Kissimmee
4.91 out of 5 average rating, 137 reviews

Lush Green Retreat 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Guest favourite
A private terrace features a spacious jacuzzi surrounded by outdoor seating. A barbecue grill is positioned nearby, with an inviting dining area visible in the background. The area is sheltered by a canopy, providing shade and comfort.
Townhouse in Kissimmee
4.81 out of 5 average rating, 138 reviews

Jacuzzi Magic Village 4 suites near Disney & 192

MAGIC VILLAGE VIEWS - 8 GUESTS - 4 SUITES - BBQ - JACUZZI - 06 MIN DISNEY Magic Village Views, new condominium, with houses of modern contemporary architecture, rooms with double height ceilings, contemporary furniture, terrace with barbecue and parking spaces in front of the unit. Well located near US-192, 6 minutes from Disney parks, 25 minutes from Universal, 26 minutes from Sea World, 3 minutes from pharmacies and Walmart. (3081 Rcf way)

Guest favourite
A spacious living area features a light-colored sectional sofa adorned with accent pillows in shades of blue and gray. A wood coffee table sits atop a patterned rug. The open kitchen is visible in the background, showcasing modern cabinetry and pendant lighting.
Townhouse in Celebration
4.92 out of 5 average rating, 109 reviews

Modern 3Bed Townhouse in the Heart of Reunion 772

Welcome to Our Stunning 3-Bedroom townhouse – Perfect for Families & Groups! Experience luxury, comfort, and top-tier hospitality in our brand-new 3-bedroom, 2.5-bathroom townhouse, designed to accommodate up to 6 guests. Whether you're planning a family vacation or a getaway with friends, our spacious retreat has everything you need for an unforgettable stay. Prime Location at Reunion Resort, just a few miles from the Disney area.

Superhost
The private pool area features clear blue water surrounded by a spacious deck. A spa is adjacent to the pool, and patio furniture is visible in the background, providing options for relaxation. A screen enclosure protects the area while allowing natural light to fill the space.
Home in Kissimmee
4.68 out of 5 average rating, 28 reviews

Getaway w/ Private Pool & SPA + BBQ | 10min Disney

Welcome to your dream vacation home! Perfectly located in Emerald Island Resort, this charming single-story 4-bedroom, 3-bath villa offers comfort, space, and privacy for families. Enjoy a private pool with spa and BBQ grill under the Florida sun, plus an open-concept layout ideal for relaxation. Just minutes from Walt Disney World, restaurants, and shops. Plus full resort amenities with heated pool, spa, gym, and clubhouse!

Guest favourite
A charming cottage features vibrant green siding and a welcoming porch with two white chairs. Lush landscaping, including palm trees and neatly trimmed shrubs, complements the exterior. A bright blue sky filled with clouds creates a cheerful backdrop.
Home in Kissimmee
4.95 out of 5 average rating, 64 reviews

Twist of Lime Cottage in Margaritaville nr Disney

Welcome to your own island-inspired oasis. Our charming cottage "Twist of Lime" is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.

Guest favourite
A modern living area is presented with large windows allowing ample natural light. A comfortable gray sofa is complemented by decorative pillows and placed in front of a glass coffee table. Two light-colored armchairs are positioned to the side, alongside a dining area featuring a stylish table.
Home in Kissimmee
4.84 out of 5 average rating, 228 reviews

4420 Le Reve 4BDRM townhouse close to Disney

Our townhouse can accommodate up to 10 people, with 4 bedrooms and 3.5 bathrooms and has a small jacuzzi for you to relax after a long day at the parks or outlets. Our property is only 10 miles to Disney’s theme parks and 15 miles to Universal Studio and major Outlets. It has many restaurants and supermarkets (Walmart, Target, Sam’s Club) nearby. Walmart Superstore is just 0.2 miles or 5 minutes walk.

Guest favourite
Home in Kissimmee
5 out of 5 average rating, 6 reviews

Luxury Villa with Private Pool Near Disney World

Live a private resort experience in this elegant 5-bedroom villa in Reunion Village, minutes from Walt Disney World 🌴 ✔ Private pool with hot tub spa ✔ High-speed Wi-Fi ✔ Self check-in with smart lock ✔ Free parking for 3 cars ✔ Fully equipped kitchen ✔ A/C and heating ✔ Golf course access 5 bedrooms, 5 private bathrooms, sleeps 10. Modern luxury decor with high-end finishes.

Guest favourite
Home in Clermont
5 out of 5 average rating, 5 reviews

Private Pool Home Near Disney | 4BR Sleeps 10

Modern designer home with private pool, perfect for families and groups near Disney. Sleeps 10 in 4 stylish bedrooms and features a chef-style quartz kitchen, elegant dining for 8, spacious living area, and a fun kids’ room. Located in a quiet upscale community just 20–25 minutes from Disney, with easy access to Universal and Orlando’s top attractions.

Guest favourite
Flat in Kissimmee
4.88 out of 5 average rating, 190 reviews

Charming Holiday Condo, Only 7 min to Disney

Step into our charming condo, where coziness awaits you! Located only 6 minutes away from the Theme Parks, prestigious Outlets, and excellent Restaurants. The property can host up to 6 guests. There is a King Size bed in the suite, two Twin Size beds in the 2nd bedroom, and one Sofa bed with a full bed in the living room.

Popular amenities for Kissimmee holiday rentals

When is the best time to visit Kissimmee?

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Avg. price$191 SGD$199 SGD$212 SGD$189 SGD$167 SGD$177 SGD$187 SGD$164 SGD$151 SGD$159 SGD$180 SGD$212 SGD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Kissimmee?

    Kissimmee has accommodations in resort areas near theme parks, private homes around Reunion and Storey Lake, and family-friendly neighborhoods with easy access to local attractions. Many spaces feature pools, spacious layouts, and outdoor amenities for group stays.

  • What are the best things to do in Kissimmee with kids?

    Families can explore fun attractions like Gatorland, ride thrilling coasters at Old Town, or enjoy large playgrounds and splash pads in city parks. Themed entertainment and interactive experiences are frequently suggested for younger visitors.

  • What are some of the best things to do in Kissimmee?

    Discover live shows and rides at Old Town, visit Gatorland for wildlife encounters, or explore regional history at the Osceola County Historical Society. The area is also known for airboat tours and vibrant outdoor markets.

  • How is the weather in Kissimmee?

    Kissimmee has mild winters around 49–72°F (10–22°C) and hot, humid summers reaching 74–92°F (23–33°C) with frequent rainfall from May through September. Lightweight clothing, sunscreen, and a rain jacket are recommended.

  • What are the best places to visit in Kissimmee?

    Popular places include Old Town for entertainment and shops, Gatorland for reptile encounters, and the Kissimmee Lakefront Park with walking trails and playgrounds. Museum enthusiasts will often find exhibits at local historical centers.

  • What are some hiking trails in Kissimmee?

    Stroll boardwalks and shaded paths at Shingle Creek Regional Park, walk lakeside trails at Kissimmee Lakefront Park, or explore nature preserves nearby. Trails often highlight local wildlife and peaceful scenery.

  • What are some family activities we can do in Kissimmee?

    Explore Gatorland’s exhibits, ride classic attractions at Old Town, or play in the splash pads at Kissimmee Lakefront Park. Family-friendly dining spots and arcades are also popular choices for shared outings.

  • What are some of the best day trip ideas from Kissimmee?

    Explore Orlando’s theme parks, stroll nature reserves around Lake Tohopekaliga, or enjoy coastal beaches for a change of scenery. You can also visit nearby state parks or experience local wildlife tours.

  • Are there any pet friendly accommodations available in Kissimmee?

    Many Kissimmee neighborhoods, including those near Central Kissimmee and the resort communities, have pet-friendly vacation rentals. Parks and outdoor spaces throughout the area make traveling with pets convenient.

  • What are some local tips for visiting Kissimmee?

    Hydrate frequently in warm months, and bring insect repellent for outdoor activities near lakes. Book popular attractions in advance and explore local eateries for regional flavors beyond the main tourist areas.

  • What is Kissimmee known for?

    Kissimmee is known for its proximity to major theme parks, distinctive wildlife experiences like Gatorland, and vibrant entertainment districts such as Old Town. Airboat rides and access to lakes add an outdoor adventure element.

  • What are the best hidden gems to explore in Kissimmee?

    Visit Shingle Creek Regional Park for quiet paddling and wildlife spotting, shop local at farmers markets, or discover history at the Osceola County Historical Society museum. Neighborhood spots often have authentic flavors and art.

  • What are the best foods to try in Kissimmee?

    Enjoy Southern-style barbecue, fresh seafood, and Latin flavors like Cuban sandwiches or empanadas at locally rooted eateries. Homemade ice cream and citrus-inspired desserts are frequently suggested, especially in summer.

  • What should I bring for a trip to Kissimmee?

    Pack lightweight clothing, sunscreen, and a hat for sun protection. A rain jacket, comfortable walking shoes, and insect repellent are useful for exploring parks and outdoor attractions.

  • What is the nightlife in Kissimmee like?

    Kissimmee has lively spots for live music, themed bars, and outdoor events in areas like Old Town. Nighttime entertainment often includes family-friendly shows and locally owned restaurants with late-night menus.

  • What are the most popular events or festivals in Kissimmee?

    Kissimmee hosts car shows, holiday parades, and cultural festivals around Old Town, with seasonal fairs and outdoor concerts often taking place in parks. Late spring and holiday weekends feature many community gatherings.

  • Are there family friendly vacation rentals in Kissimmee?

    Family-friendly vacation rentals are available throughout Kissimmee, particularly in resort-style neighborhoods and private home communities. Many have amenities like pools, recreation rooms, and easy access to parks and attractions.

  • When is the best time to visit Kissimmee?

    Late autumn and early spring are often recommended, with milder temperatures and smaller crowds. Summer brings lively local events and frequent afternoon rain, while winter stays mild and sunny.

Quick stats about holiday rentals in Kissimmee

  • Total holiday rentals

    Explore 7,260 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 267,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,840 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 1,160 rentals that welcome pets

  • Holiday rentals with a pool

    6,460 properties feature pools

  • Rentals with dedicated workspaces

    4,030 properties have a dedicated workspace

  • Wifi availability

    7,170 of Kissimmee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Lake access across Kissimmee rentals

  • 4.7 Average rating

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee