Holiday houses in Kissimmee

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Top-rated holiday rentals in Kissimmee

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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, 160 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 exterior of a single-story townhome is depicted, featuring a sidewalk leading to the entrance. Neatly trimmed shrubs and a small tree are present in the front yard, with a grassy area surrounding the home. A clear sky is visible in the background.
Townhouse in Orlando
4.97 out of 5 average rating, 116 reviews

Convenient Townhouse

Single-story townhome. A small conservation area serves as a background to the back porch. There is one parking space right in front of the home. It is conveniently located 15 minutes from the Orlando International Airport; 12 minutes from Gatorland, 25 from Walt Disney World, Universal Studios; and 1 hour from Kennedy Space Center and Cocoa Beach. USTA campus 20 minute drive via 417. Eateries, grocery stores, and pharmacies are within a 5 minute drive. 1 room is used for storage (not shown)

Top Guest favourite
Tiny home in Kissimmee
5 out of 5 average rating, 34 reviews

Casa Bonita

Experience a unique and romantic retreat in our charming tiny home—ideal for couples or solo travelers seeking peace and tranquility. Nestled in a serene neighborhood, it features a cozy full-size bed, a fully equipped compact kitchen, and a peaceful outdoor space. Enjoy morning coffee on the patio, stargaze at night, and embrace tiny living with modern comforts. Plus, you’re just minutes away from top attractions like Disney, Epic Universe, SeaWorld, Volcano Bay, and the Convention Center.”

Top Guest favourite
Guest suite in Orlando
4.96 out of 5 average rating, 143 reviews

Cozy Private Studio Suite • Near Theme Parks

Spacious private-entrance studio guest suite (private BR/BA) less than 20 min to Disney, Universal, Orlando theme parks 🎢, major hospitals 🏥 & MCO ✈️. • Walk to groceries & restaurants, unwind in the hammock, and stream 📺 Disney+/Hulu/ESPN+. • Quick access to 417, I-4 & FL Turnpike for easy park hopping. • See Kennedy Space Center launches 🚀 (53 mi away). • Pet-friendly (fee) 🐕 with fenced backyard. • Private indoor space; patio occasionally accessed for maintenance & friendly pets.

Guest favourite
A door with a keypad entry system is shown, leading into the living space. Framed artwork adorns the wall in soft colors, while green curtains frame a nearby window. A glimpse of a bed is visible, covered with a textured blue bedspread.
Guest suite in Kissimmee
4.94 out of 5 average rating, 171 reviews

It's too much like a elegant mini-hotel (6)

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. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

Top Guest favourite
A brightly painted tiny home is showcased against a serene backdrop. The exterior features red and yellow hues with a blue door and window. Two blue chairs are positioned beside a small table, creating an outdoor seating area surrounded by lush greenery.
Guesthouse in Kissimmee
4.96 out of 5 average rating, 103 reviews

Orlando Private Tiny Guest House

*Quiet, safe neighborhood Premium location *20 minutes to Orlando Airport *20 minutes to Disney parks & Disney Springs *25 minutes to Universal Studios & CityWalk *7 minutes to shopping plaza with top outlets and diverse dining *5 minutes to super Walmart *Local minimarkets. Inside your tiny home: *Queen-size bed *Coffee, fridge & microwave *Private entrance + patio *Modern shower *Air conditioning, Wi-Fi & Smart TV *Need transportation or special arrangements? Let us know

Top Guest favourite
A private balcony features two black chairs positioned for relaxation. Below, a green landscape borders a calm waterway, with trees lining the banks. Industrial buildings can be seen in the distance under a clear blue sky.
Apartment in Kissimmee
4.98 out of 5 average rating, 52 reviews

Modern King Apt w Water view, Pool Gym Near Parks

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

Top Guest favourite
A cozy bedroom features a tufted gray headboard above a neatly made bed with white linens. Decorative pillows are arranged on the bed, and whimsical letters spelling 'DREAM' adorn the wall above. Two bedside tables with lamps provide a soft glow.
Guesthouse in Four Corners
4.98 out of 5 average rating, 511 reviews

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

Guest favourite
A spacious kitchen area features dark wooden cabinetry and granite countertops, with appliances visible including a refrigerator and a dishwasher. A dining table can be seen in the background, surrounded by stylish chairs. Large windows allow natural light to fill the adjoining living space.
Home in Orlando
4.81 out of 5 average rating, 253 reviews

Perfect location near Sea World and Disney

Welcome to our perfectly located 2 bedrooms, 2 bathrooms condo on international drive. We are located in the heart of Orlando. Only a few minutes from most major attractions that Orlando as to offer. We are 2.5 miles from Sea World, 5 miles from Disney World main entrance, 2.7 miles from Orange County Convention center and 1.8 miles from the Vineyard vine outlet for your shopping experience.

Guest favourite
A cozy bedroom features a spacious bed dressed in white linens, flanked by two nightstands. A decorative mirror is mounted above the bed, reflecting light. A small seating area includes a white wicker chair, while artwork adorns the adjacent wall, enhancing the calming design.
Apartment in Kissimmee
4.92 out of 5 average rating, 49 reviews

Relaxing Escape w/ Private Patio near MCO & Parks

Relájate en esta escapada única y tranquila, ubicado en Kissimmee , es un espacio acogedor y confortable para que pases unos días inolvidable, nuestro espacio tiene un amplio dormitorio y cuenta con baño , cocina y un amplio patio para que puedas compartir. Los huéspedes tienen acceso gratuito , además se encuentra cerca de los parques principales de Disney y otras atracciones de Orlando.

Guest favourite
Townhouse in Kissimmee
5 out of 5 average rating, 14 reviews

Casa Resort Storey Lake a minutos de Disney y Epic

Espectacular casa en Storey Lake Resort, con 4 habitaciones para 12 personas y piscina privada. Perfecta para familias que buscan comodidad y diversión. Acceso a río lento, piscinas, toboganes, mini-golf y gimnasio. A solo 10–15 min de Disney, 20–25 min de Universal y 15–20 min de SeaWorld. Ubicación ideal para unas vacaciones inolvidables.

Top Guest favourite
A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.
Condo in Kissimmee
4.84 out of 5 average rating, 147 reviews

Stunning view, near Disney.

Very comfortable unit with a stunning view of the pond. Full equipped kitchen , close to everything (grocery, shopping,3 miles from Disney, sea world, universal, etc). Shuttle to Disney and Universal studio. Free access to all amenities to the hotel beside ( mini putt, pools, zip line ($), hot tubs, starbucks). Just waiting for you.

Popular amenities for Kissimmee holiday rentals

When is the best time to visit Kissimmee?

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Avg. price$237 NZD$243 NZD$253 NZD$247 NZD$218 NZD$232 NZD$245 NZD$215 NZD$198 NZD$208 NZD$235 NZD$277 NZD
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 7,330 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 262,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    6,190 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,210 rentals that welcome pets

  • Holiday rentals with a pool

    6,620 properties feature pools

  • Rentals with dedicated workspaces

    4,060 properties have a dedicated workspace

  • Wi-Fi availability

    7,280 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