Vacation rentals in Kissimmee

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Top-rated vacation rentals in Kissimmee

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

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Superhost
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Disney Luxury 5bedroom 4bath Resort WaterPark Free

Ao lado do complexo Disney. Resort encantador com Parque Aquático grátis, salão de jogos/arcade, cinema grátis, bar de piscina, lanchonete e muito mais. Belissima casa, toda reformada com 5 quartos confortáveis e bem equipados para até 12 hóspedes. Muito conforto 4 banheiro Cozinha completa Sala de estar ampla Piscina privativa no fundo da casa com Screen/tela fechados, churrasqueira privativos. Estacionamento gratis. A poucos minutos de carro dos parques da Disney, Universal e outras atrações.

Top guest favourite
The living area features a modern design, showcasing a large wall-mounted television opposite a comfortable seating arrangement on a tiled floor. Natural light pours in through expansive windows, enhancing the spaciousness. Decorative plants add a touch of greenery, while stylish curtains frame the view outside.
Apartment in Kissimmee
4.98 out of 5 average rating, 101 reviews

3161-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 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, 151 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
Tiny homes in Kissimmee
5 out of 5 average rating, 30 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
The swimming pool is illuminated with a calming blue glow, reflecting the evening light. Lush landscaping is visible outside the screened patio, and the entrance to the private suite can be seen through spacious glass doors.
Guest suite in Davenport
4.95 out of 5 average rating, 311 reviews

Oak Promenade Peaceful Studio with Private Pool

‘The Studio’ is your peaceful retreat steps away from your own sparkling private pool! You’ll be located in an elegant cul-de-sac of a quiet neighborhood - a perfect way to wind down from long, busy days at theme parks. 20 minutes from Disney World 27 minutes from Universal 25 minutes from Sea World If you are traveling with friends and/or family, we also have another studio right next door! airbnb.com/h/thousandoakspeacefulstudio This is a safe space. You are welcome here!

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, 133 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!

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, 170 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. All of my houses have hosted countless friendly and courteous guests from Brazil. We will always welcome you!

Guest favourite
A spacious living area showcases a gray sofa adorned with decorative pillows. A dark rug sits beneath the seating arrangement, while a dining set with light wooden chairs and a round table is visible in the adjacent open-concept kitchen. A ceiling fan and floor lamp provide ambient lighting.
Apartment in Kissimmee
4.87 out of 5 average rating, 93 reviews

Relax in Cozy Apt 1/1 near to Disney

Your family will be close to everything when you stay at this centrally located accommodation. It is a beautiful completely renovated property, new on Airbnb, it is located on the third floor, accessed by stairs, there are no elevators, please evaluate this information carefully before booking, it is fully equipped for you to enjoy of your stay You will be very close to the main theme parks of the city such as Disney World and Universal Studios.

Guest favourite
A pool area is enclosed by a screened structure, featuring a sparkling blue pool with a connected hot tub. Tropical palm trees are visible in the background, adding a touch of greenery to the tranquil setting.
Guest suite in Kissimmee
4.84 out of 5 average rating, 622 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers! 😀 We offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We offer our home to travelers only-we do not accept local reservations.

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, 507 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 large outdoor pool is surrounded by lounge chairs and shade trees. The pool area features a covered structure, and a connected whirlpool is visible. Apartment buildings are seen in the background against a clear blue sky.
Apartment in Kissimmee
4.89 out of 5 average rating, 392 reviews

3BR/2Bath Spacious condo 15min to Disney

Excellent location! Usually, it 15 minutes to get to Disney main gate and 25 minutes to get to Orlando international airport. Nearby most Orlando attractions. The house easily fits a moderate size group it boasts 3 bedrooms 2 baths and a beautiful view balcony. This residence is located in a resort with a fitness room and a beautiful pool. The house made to feel like your home.

Top guest favourite
A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.
Condo in Orlando
4.98 out of 5 average rating, 231 reviews

Lakefront Resort Condo near Disney and Universal

Your magical getaway starts here—just minutes from Disney & Universal Parks ! Relax on your balcony overlooking stunning Lake Bryan, splash in the heated pool, sip at the Tiki bar, and stream your favorite shows with HBO & Netflix. Concierge for park tickets, free parking, 24-hr security. No deposit, no extra fees—just fun, sun, and memories waiting!

Popular amenities for Kissimmee vacation rentals

When is the best time to visit Kissimmee?

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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.

All about Kissimmee

Located in central Florida, Kissimmee is well situated near some of the most sought-after attractions in the state. Being so close to the Walt Disney World Resort, Universal Orlando Resort, and LEGOLAND Florida parks ensures that this city is popular with families and theme-park fans alike. Kissimmee has its own set of charms to entice visitors, including easy access to the Florida Everglades, the Kennedy Space Center, and many aquatic attractions. You can spend jam-packed days enjoying the company of fairy-tale creatures and riding thrill rides, then change it up with visits to the natural world and dreams of reaching for the stars in outer space. The city has its share of nationally known dining options to cater to visitors from around the world, including entertainment districts that combine the best in food, shopping, and fun. Whether you’re looking for magical lands, family fun, or a wide variety of entertainment options, Kissimmee will deliver an unforgettable holiday experience.

What are the top things to do in Kissimmee?

Immerse Yourself in Magical Worlds

Kissimmee is minutes from some of the most popular theme parks in the world. From exploring the four Walt Disney World Resort parks to channeling wizarding magic and superhero power at Universal Orlando Resort and building vacation memories at LEGOLAND Florida, central Florida’s theme parks are not to be missed.

Kennedy Space Center Visitor Complex

Defy gravity and reach for the stars at this gateway to space exploration. The center features behind-the-scenes tours of launch sites and spaceflight facilities, a walk-through rocket garden, astronaut training simulation rides, and the chance to get up close to the Space Shuttle Atlantis.

Florida Everglades

Kissimmee is near Shingle Creek, the headwaters to the Florida Everglades, sometimes called the Sea of Grass. Kayaking in the calm waters beneath a quiet forest of cypress trees is an ideal way to learn more about this unique ecosystem and the many birds, frogs, and alligators who make it their home. Or take a swamp tour on an airboat and leave the driving to someone else.

Quick stats about vacation rentals in Kissimmee

  • Total vacation rentals

    Explore 7,330 vacation rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee vacation rentals start at $27 CAD per night before taxes and fees

  • Verified guest reviews

    Over 262,660 verified reviews to help you choose

  • Family-friendly vacation rentals

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

  • Pet-friendly vacation rentals

    Find 1,210 rentals that welcome pets

  • Vacation rentals with a pool

    6,620 properties feature pools

  • Rentals with dedicated workspaces

    4,060 properties have a dedicated workspace

  • Wifi availability

    7,280 of Kissimmee vacation rentals include wifi 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