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Vacation rentals in Kissimmee

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Quick stats about vacation rentals in Kissimmee

  • Total vacation rentals

    Explore 6,930 vacation rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee vacation rentals start at ﺩ.ﺇ 73 per night before taxes and fees

  • Verified guest reviews

    Over 284,240 verified reviews to help you choose

  • Family-friendly vacation rentals

    5,730 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 1,230 rentals that welcome pets

  • Vacation rentals with a pool

    6,140 properties feature pools

  • Rentals with dedicated workspaces

    3,790 properties have a dedicated workspace

  • Wi-Fi availability

    6,840 of Kissimmee vacation rentals include wi-fi 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

Top-rated vacation rentals in Kissimmee

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

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Top guest favorite
A resort-style water complex is surrounded by lush landscaping and palm trees. The winding pool features clear, inviting water with lounge areas and shaded cabanas. Bright blue skies filled with clouds create a serene backdrop for this recreational oasis.
Townhouse in Kissimmee

Disney 5BR • Private Pool Free Heat • Pet Friendly

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

LocationFamilyCheckout

4.98 out of 5 average rating, 288 reviews
Top guest favorite
Home in Kissimmee

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

ValueFamilyTV

4.9 out of 5 average rating, 129 reviews
Guest favorite
Home in Kissimmee

MoanaTheme| YES Pets| Heated POOL & SPA| Disney

Welcome to the Moana Tiki Cabana, a tropical-oasis located in the exclusive Encore gated resort close to Disney! This 5-bedroom, 4-bath retreat offers a unique, playful Moana design, a fully stocked kitchen with FREE snacks, coffee, water, Fast Wi-Fi, 6 Smart TV’s and Games. Our private backyard features a heated pool, hot tub, BBQ grill, and dining area – perfect for Vacationers! With plenty of space for up to 12 guests, it’s an ideal pet friendly getaway for families with a crib & high chair.

LocationValueBathroom

4.95 out of 5 average rating, 100 reviews
Top guest favorite
Townhouse in Kissimmee

6 miles from Disney ! Private pool

This Beautiful newly renovated 3 bedroom 2.5 bathroom luxury townhouse has a private pool with complimentary resort facilities. The house is close to the Resort and Clubhouse, which has a lobby/reception, snack bar, all-year heated pools, training facilities, and a game room. It is 15 minutes from all Disney parks and close to Orlando attractions. Orlando International Airport is just 40 minutes from the home. Very relaxing and cozy. Newly renovated with new appliances and furniture.

FamilyLocationCleanliness

4.86 out of 5 average rating, 326 reviews
Guest favorite
The image showcases various themed sleeping areas within the vacation home. A Superhero Room displays colorful walls with superhero motifs, while the Princess Room features castle imagery. A cozy nook with a bunk bed is visible, alongside arcade machines that add to the playful environment.
Townhouse in Kissimmee

Magical Hideaway - 15 min to Disney - Storey Lake

Welcome to The Magical Hideaway! Bring your family an immersive experience into our Disney-themed vacation home in Storey Lake community. Our home includes a specially themed Princess and Superhero rooms. Dive into fun at the resort pool with a lazy river and water slides. Enjoy your own plunge pool and our photo-op green wall. Entertainment includes 4 Roku TVs, Disney board games, and puzzles. We've also got you covered with a stroller, crib, and highchair provided.

FamilyLocationParks

4.91 out of 5 average rating, 157 reviews
Top guest favorite
A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.
Home in Kissimmee

10 Minutes to Disney King Bed, Heated Pool, Arcade

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

LocationFamilyCheck-in

4.98 out of 5 average rating, 115 reviews
Top guest favorite
A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.
Home in Kissimmee

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much More. Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

FamilyValueWifi

4.94 out of 5 average rating, 169 reviews
Top guest favorite
A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.
Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

FamilyValueHospitality

4.96 out of 5 average rating, 122 reviews
Guest favorite
Home in Kissimmee

Modern 12 BR 11.5 BA, Sleeps 32, 15 mins to Disney

Welcome to this modern 12-bedroom, 11.5-bath home—perfect for your next family getaway! Comfortably sleeping up to 32 guests, this centrally located retreat is just 15 minutes from the Disney parks. Enjoy fantastic amenities including a private pool and spa, a home theater for movie nights, and a fun-filled game room. With plenty of space and entertainment for all ages, it’s the ideal spot for family reunions, group vacations, and special get togethers.

FamilyLocationGrill

4.86 out of 5 average rating, 102 reviews
Top guest favorite
Condo in Kissimmee

Near Disney • 4BR • Perfect for Families

Guests love this home! It’s usually fully booked! Location is incredible! Heart our property and save it to your wishlist! IMPORTANT: parking available only for one car. 9 min - Hollywood Studios (6 mi) 10 min - Animal Kingdom (8 mi) 12 min - Disney Springs (5 mi) 15 min - Magic Kingdom (10 mi) Just 3’ from Walmart, Publix, and a big strip mall full of restaurants, grocery stores, and shopping! Experienced host, 10 years on Airbnb!

ValueFamilyAccess

4.97 out of 5 average rating, 269 reviews
Guest favorite
Home in Kissimmee

The Real Florida Whispering Oaks

The Oaktree home is a favorite among returning guests. Once you have stayed in this home you cannot wait to return. The spacious pool /spa and deck area, game room and provides all you could ask for to make your stay one to remember. Recently remodeled kitchen with updated appliances make this home shine! Partially fenced in yard with no rear neighbors offer you a quiet retreat. T.V. on pool deck! Complimentary Hot Tub Heat!

LocationValueOutdoor spaces

4.79 out of 5 average rating, 136 reviews
Superhost
A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.
Home in Buenaventura Lakes

Villa Resort Club

Welcome to Villa Resort Club! Lovely 4BR/2.5BA for 8 with a screened private pool and game room. Full kitchen, workspace, washer/dryer, parking, and Wi-Fi. Pet-friendly. Minutes from Disney. Quiet, comfy home base! Welcome to Villa Resort Club! House with 4 bedrooms/2.5 bathrooms for 8, pool with enclosure and games. Full kitchen, workspace, washer/dryer, parking, Wi-Fi. Pets OK. Minutes from Disney. Quiet and comfortable!

ValueFamilyGetting around

4.87 out of 5 average rating, 189 reviews

Popular amenities for Kissimmee vacation rentals

Self check-inBeachfrontLake accessGymBBQ grill

Stay near Kissimmee's top sights

Kissimmee Lakefront Park

345 locals recommend

Walmart Supercenter

991 locals recommend

Gatorland

944 locals recommend

Medieval Times Dinner & Tournament

582 locals recommend

Bellavida Resort

16 locals recommend

Terra Verde Resort

6 locals recommend

Private vacation rentals in Kissimmee

Top guest favorite
Home in Kissimmee

Private Pool + Spa Game Room •4m Disney •Pinball

FamilyValueHospitality

4.93 out of 5 average rating, 166 reviews
Superhost
Townhouse in Kissimmee

Excelent 4 stes jacuzzi near Disney &192 (3081)

FamilyLocationIndoor spaces

4.79 out of 5 average rating, 147 reviews
Guest favorite
A modern movie theater features a large 155-inch screen displaying a Disney logo, surrounded by plush recliners designed for comfort. The room is illuminated with soft blue lighting, creating a cozy atmosphere for movie nights or gaming sessions.
Villa in Kissimmee

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

LocationValueKitchen

4.86 out of 5 average rating, 148 reviews
Top guest favorite
Home in Kissimmee

Lakeview 15 Min to Disney Pool Home 4BR/3BA

ValueFamilyAccuracy

5.0 out of 5 average rating, 8 reviews
Top guest favorite
Townhouse in Kissimmee

Disney Theme Rooms | Private Pool | Storey Lake

FamilyLocationHospitality

5.0 out of 5 average rating, 48 reviews
Guest favorite
Home in Kissimmee

Luxe Family Escape | Pool Oasis Near Disney

FamilyLocationHospitality

5.0 out of 5 average rating, 8 reviews
Superhost
Home in Clermont

2026 Luxury 10BR Themed Villa at Windsor Cay

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 3 reviews
Top guest favorite
Apartment in Kissimmee

Haunted Mansion-inspired Ghoulish Sanctuary

ValueFamilySleep quality

4.96 out of 5 average rating, 50 reviews

Kissimmee beach vacation rentals

Top guest favorite
The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.
Hotel room in Orlando

PentHouse Suite with 2X View

LocationFamilyComfort

4.96 out of 5 average rating, 205 reviews
Guest favorite
Condo in Orlando

Luxury PH Direct Disney Fireworks View from Apt

FamilyLocationAmenities

4.9 out of 5 average rating, 103 reviews
Guest favorite
The room features a spacious bed with a dark headboard and a blue accent pillow. A small table with two chairs is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through a window dressed with sheer curtains.
Home in St. Cloud

Comfy Studio w/ private Entrance

FamilyValueView

4.95 out of 5 average rating, 132 reviews
Superhost
Villa in Clermont

Family Friendly w/ KING bed Sleeps 4 midterm avail

FamilyLocationAccuracy

4.82 out of 5 average rating, 108 reviews
Superhost
A mid-century home is framed by mature oak trees, providing shade to the grassy front yard. Large windows reflect the natural light, highlighting the clean lines of the exterior. The tranquil setting is complemented by the beauty of the surrounding landscape.
Home in Windermere

Water Front Haven

LocationFamilyParks

4.93 out of 5 average rating, 29 reviews
Top guest favorite
Aerial view of the resort showcases a large swimming pool surrounded by lush greenery and sandy areas. Tiki huts provide shaded seating, while blue loungers are arranged neatly across the beach area, creating a relaxed outdoor space for guests.
Villa in Davenport

1st level Pool/Beach Disney Area

FamilyLocationTV

4.98 out of 5 average rating, 60 reviews
Guest favorite
Apartment in Orlando

UniqueStay w Lakeview/DisneyFireworks/WaterSports

LocationFamilyPool

4.92 out of 5 average rating, 12 reviewsA vibrant themed game room features colorful Super Mario decor on the walls, creating a playful environment. An air hockey table is positioned in the foreground, with comfortable seating visible in shades of yellow. A large TV screen is mounted on the blue wall, enhancing the entertainment options.
Home in Kissimmee

Exclusive 8BR Themed Villa • Private Pool Retreat

ValueLocationLayout

4.76 out of 5 average rating, 34 reviews

Family friendly vacation rentals in Kissimmee

Superhost
Condo in Kissimmee

SpongeBob themed studio w/ pool & TV

ValueFamilyCleanliness

4.87 out of 5 average rating, 128 reviews
Top guest favorite
A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.
Condo in Orlando

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

ValueFamilyHot tub

4.95 out of 5 average rating, 196 reviews
Guest favorite
An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.
Condo in Kissimmee

WH Condo. Pool/Waterpark and close to Disney!

LocationFamilyGetting around

4.85 out of 5 average rating, 189 reviews
Top guest favorite
The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.
Townhouse in Kissimmee

Lake View - 5 Miles to Disney!

FamilyLocationCheckout

4.99 out of 5 average rating, 194 reviews
Top guest favorite
Home in Kissimmee

Disney-Inspired Suites • Game Room • Summerville

ValueLocationPets

4.95 out of 5 average rating, 193 reviews
Top guest favorite
Home in Davenport

Magical Pool Villa-close to Disney Game/movie Room

ValueLocationCleanliness

4.91 out of 5 average rating, 180 reviews
Top guest favorite
Condo in Kissimmee

Magic Condo at a Resort Near Disney

FamilyLocationCheckout

4.98 out of 5 average rating, 204 reviews
Guest favorite
Home in Kissimmee

6BR Family Fun Starts Here with Pool& Games 243541

ValueFamilyNearby

4.88 out of 5 average rating, 144 reviews

When is the best time to visit Kissimmee?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 547ﺩ.ﺇ 569ﺩ.ﺇ 606ﺩ.ﺇ 621ﺩ.ﺇ 529ﺩ.ﺇ 547ﺩ.ﺇ 536ﺩ.ﺇ 470ﺩ.ﺇ 433ﺩ.ﺇ 455ﺩ.ﺇ 514ﺩ.ﺇ 606
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.

All about Kissimmee

Less than 30 minutes south of Orlando, the central city of Kissimmee makes for an ideal home base for visiting Florida’s most popular theme parks. The city sits on the northwest corner of Lake Tohopekaliga, also known as Lake Toho, which stretches across Kissimmee for four miles. Flat, grassy terrain complemented by tall palm trees surrounding the water make Lake Toho the unofficial centerpiece of Kissimmee. Many local activities revolve around the lake, from bass fishing to bird watching and scenic walks through its lakefront parks.

Tall mangrove trees sprouting up from the wetlands mark the official start of the infamous Florida Everglades at Kissimmee’s Shingle Creek Regional Park. These protected wetlands stretch for more than a million acres from Kissimmee to the tip of South Florida, finally emptying into the Gulf of Mexico. The park’s grassy terrain leads you to long, overwater docks hovering over the freshwater marshes, but visitors be warned: this lush foliage also provides perfect coverage for one of Kissimmee’s scaly residents, the alligator. The city takes great measures to ensure that they never cross paths with humans, but do heed the signs and do your bird spotting on the decks. On a clear day, you might find a sandhill crane or the bright pink roseate spoonbill.

What are the top things to do in Kissimmee?

Kissimmee Lakefront Park

The one-mile walking trail at the Kissimmee Lakefront Park is an easy walk or bike-friendly path over flat, grassy terrain. The trail follows the north shore of Lake Tohopekaliga, and at opposite ends of the trail, you can make stops at the Big Toho Marina and the eclectic Monument of States Memorial. This quirky memorial is made with stones from each of the 50 states that make up the United States.

Museum of Military History

Exhibitions featuring historic relics help tell the story of America’s military endeavors, beginning with the Revolutionary War and ending in the present day. Each of the five military branches is included too. Authentic, donated artifacts representing each major military event are on display for visitors to take in, from muskets used in 1775 to World War II service vehicles. Guided tours are often led by military veterans.

Twin Oaks Conservation Area

The 370-acre Twin Oaks Conservation Area along Lake Tohopekaliga preserves Floria’s native wildlife habitats. Tall, untamed grass pokes through the park’s freshwater marshes, and overwater piers jut out over the marshlands for visitors to take a closer look at the landscape and its inhabitants. The best wildlife lookout point is at the park’s main, elevated viewing platform, where you may be able to spot one of Florida’s most well-recognized reptiles, the alligator, or even a bald eagle.

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