Holiday houses in Kissimmee

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Top-rated holiday rentals in Kissimmee

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Top Guest favourite
A cozy sleeping area is outfitted with a full size bed featuring a neutral-toned bedspread, complemented by decorative pillows. A small sofa sits nearby, adorned with striped and solid pillows. Barn-style sliding doors lead to a bathroom, while a woven rug adds texture to the floor.
Tiny home in Kissimmee
5 out of 5 average rating, 22 reviews

Casita bonita

You'll love this unique and romantic escape of our tiny home — perfect for couples or solo travelers seeking a peaceful retreat. Nestled in a quiet neighborhood, this space features everything you need: a comfy full size bed, a compact but fully equipped kitchen, and a relaxing outdoor area. Enjoy morning coffee on the back patio, stargazing at the stars and the simplicity of tiny living with modern comforts. Just minutes from local attractions, Disney, Epic universe, Sea World, Volcano Bay, etc

Top Guest favourite
A modern living area features a sectional sofa adorned with decorative pillows and a coffee table at the center. A large wall-mounted television provides entertainment options, while expansive glass doors open to a balcony showcasing scenic views. Bright lighting enhances the open and airy ambiance.
Apartment in Kissimmee
4.95 out of 5 average rating, 62 reviews

3191-307 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, 137 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, 59 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.

Top 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
4.95 out of 5 average rating, 75 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, 76 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
The recreation area is designed with vibrant blue lighting and themed decor. It features a pool table, arcade games, and a commercial air hockey table. The walls are adorned with popular character themes, including Super Mario and Avengers, creating an engaging and playful atmosphere.
Home in Kissimmee
4.98 out of 5 average rating, 99 reviews

Dream Vacation w/Avengers, Star Wars, & Mario Kart

Experience the magic of Disney World, Universal Studios, and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in Storey Lake Resort, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, Universal Studios, Sea World, Premium Outlet Malls, and beyond! This modern property is focused on providing an unforgettable and exceptional family centric vacation experience!

Top Guest favourite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 115 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Top Guest favourite
A bright and open living space features comfortable seating arranged around a large flat-screen TV. A dining area with a round wooden table is surrounded by woven chairs, while the kitchen showcases modern cabinetry and stainless steel appliances, illuminated by pendant lighting.
Townhouse in Four Corners
5 out of 5 average rating, 74 reviews

New Modern Home near Disney in Orlando

Located only a few minutes from Disney World Orlando, Theme Parks, Disney Springs and unique dining experience, your stay will be one to remember. You will be entertained for days with Orlando’s attractions, parks, golf courses, lakes, trails, malls, restaurants, and nearby cities and beaches With 6 beds and a sofa bed, there's more than enough room for the whole group to get a comfortable night's rest from the day's adventures

Top Guest favourite
A modern kitchen is highlighted by sleek granite countertops and energy-efficient stainless steel appliances. Four adjustable stools are situated at a kitchen island, offering a comfortable dining or working space. The well-lit area features white cabinetry and large windows that let in natural light.
Apartment in Orlando
5 out of 5 average rating, 54 reviews

Charming King Suite, Near Universal & Pet-Friendly

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in Orlando! This chic and cozy apartment offers the ideal base for your Florida adventure. It combines comfort with convenience, featuring easy access to nearby theme parks, shopping, and dining options. Relax with resort-style amenities in the charming community. The whole apartment will be yours and NOT shared. Please reach out for potential multi-day discounts.

Top Guest favourite
A spacious bedroom features a comfortable bed with decorative pillows and a modern ceiling fan. An open kitchen area showcases stylish cabinetry and stainless steel appliances. A living area is equipped with ample seating and large windows allowing natural light. Another bedroom is similar in style with neutral tones.
Apartment in Kissimmee
4.86 out of 5 average rating, 96 reviews

Luxury Resort Style Condo Near Disney-103

A 5-star stay 3bed/ 2.5bath resort-style condos where you’ll enjoy unprecedented access to amenities that are fun for the entire family. Lounge by multiple community pools and have fun. This relaxing family-friendly home is fully equipped with all modern conveniences and has everything you will need to make your dream Orlando vacation a reality! We have multiple units therefore all photos are not exact to this unit.

Top Guest favourite
A gold keypad lock is mounted on a white door frame, with the blurred outline of a spacious sleeping area behind it. Soft lighting from a nearby table lamp casts a warm glow, while green curtains hang in the background.
Guest suite in Kissimmee
4.97 out of 5 average rating, 165 reviews

It's too much like a elegant mini-hotel (3)

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.

Popular amenities for Kissimmee holiday rentals

When is the best time to visit Kissimmee?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$247 NZD$254 NZD$265 NZD$258 NZD$228 NZD$242 NZD$256 NZD$224 NZD$207 NZD$221 NZD$237 NZD$279 NZD
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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 7,290 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, Beachfront and Gym 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