Vacation rentals in Kissimmee

4.91 out of 5 average rating, 154 reviews

Magical Pool Villa-close to Disney Game/movie Room

The whole family will have fun in our Magical Disney Home where the Magic of Mickey Mouse,Toy Story, Frozen and Minion bedrooms with Sensor Songs when you walk in each room, uv and Led lights.Color changing Led lights in pool + bbq area, loungers for sun tanning.This Villa has Disney Hand UV light Painted by a local artist and a Game room with air hockey arcade, your children will feel the Magic as soon as they walk in the home, from smell to sound to sight This is it!Your Magical Dream Vacation

A private pool area is featured, showcasing clear water reflecting sunlight. Cozy seating, including chairs and a table, is positioned under a covered patio, while a basketball hoop is mounted nearby. Sun loungers are arranged on the pool deck, inviting relaxation.

4.91 out of 5 average rating, 104 reviews

Gorgeous 6BR PetFriendly Home Pool | Disney - 2004

Brand new luxury home with a private backyard, pet friendly, NO CARPET anywhere, located at world-renowned Solara Resort. Over 3000sf of A/C area, featuring 6 bedrooms, 4.5 bathrooms, game room, private pool and spa, and full access to resort amenities 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 25 Minutes away from Universal Studios 25 Minutes away from International Dr PLEASE MAKE SURE TO READ OTHER THINGS TO NOTE FOR HOUSE RULES

4.83 out of 5 average rating, 188 reviews

Townhouse in Kissimmee

Fantasy World The Dalmatians Villa, Free Waterpark

Discover our charming Dalmatian House at Fantasy World Villas, minutes from Disney, Universal & Sea World. This modern 2-bed villa features a 101 Dalmatians themed room, king-size bed in the master, full kitchen, laundry, private patio, free Wi-Fi & parking. Enjoy resort amenities: heated pools, hot tubs, lazy river, water slides, tiki bar, gym, playground, sports courts, and more. Walk to restaurants & find grocery stores nearby. Experience a magical stay in this captivating retreat! Book Now!

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 120 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

4.99 out of 5 average rating, 193 reviews

A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.

Cottage in Kissimmee

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

4.94 out of 5 average rating, 220 reviews

Two wooden cabins are positioned under tall trees, reflecting on the calm water's surface. A small seating area with bright blue chairs and a fire pit is situated on the grassy shore, providing a relaxed outdoor space, while the surrounding nature complements the serene setting.

Home in Clermont

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

Home in Buenaventura Lakes

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.

4.96 out of 5 average rating, 119 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

4.93 out of 5 average rating, 103 reviews

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

Villa in Citrus Ridge

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.

4.96 out of 5 average rating, 201 reviews

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

4.98 out of 5 average rating, 126 reviews

The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.

Cottage in Citrus Ridge

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage 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. All Pets Must Be Preapproved :)

The exterior of the pool house reveals a welcoming facade with a well-maintained lawn. A screened-in pool area showcases a spacious pool surrounded by tile flooring. The interior features a game room with a billiards table and air hockey, highlighted by modern entertainment options.

4.84 out of 5 average rating, 135 reviews

Pool House in Kissimmee

Quiet and spacious pool house in Kissimmee Florida, 20 minute away from Disney / Universal / Acquatica / SeaWorld theme parks. - 4 bedrooms - 2 bathrooms - Dining Room - Family Room - Kitchen - Double car garage - BBQ - Pool (heater optional) - Security Cameras Outside Only - WiFi 400 MBPS Pool Heater: If you want to use the heater please contact owner This will be your best vacation stay in Kissimmee / Orlando.

4.95 out of 5 average rating, 176 reviews

A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.

Villa in Citrus Ridge

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

🏡 **Welcome to Disney Serenity** – a family-friendly villa near Disney World! Enjoy a **private heated pool**, **game room**, and **cinematic home theater**. Plus, access resort amenities like a **lazy river, gym, and tiki bar**. **Wheelchair-friendly** and perfectly located for Disney & Universal adventures. Book now for a magical stay! ✨

Popular amenities for Kissimmee vacation rentals

Self check-in

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

Stay near Kissimmee's top sights

Kissimmee Lakefront Park

332 locals recommend

FantasyWorld Resort

7 locals recommend

Silver Spurs Arena

22 locals recommend

Walmart Supercenter

978 locals recommend

Lake Buena Vista Factory Stores

331 locals recommend

Kissimmee Gateway Airport

15 locals recommend

Private vacation rentals in Kissimmee

5 out of 5 average rating, 4 reviews

Game Room|Movie Room|Free Pool Heat&BBQ|Sleeps 23

5 out of 5 average rating, 31 reviews

The spacious screened porch features warm lighting and a cozy dining area, surrounded by lush greenery. Several reclining chairs with ottomans offer relaxation, while decorative ground lights highlight the landscape. French doors connect the porch to the interior, creating a welcoming open space.

Townhouse in Kissimmee

The Sandy Gator

4.98 out of 5 average rating, 55 reviews

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

Apartment in Kissimmee

Modern Condo: 10 Min to Disney + Fireworks Views!

5 out of 5 average rating, 19 reviews

15BD - Sleeps 30 - Themed - 15 mins to Disney

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

4.98 out of 5 average rating, 82 reviews

Large Private Home on Golf course by Disney

Galactic Star Wars Experience•8 BRM, Sleeps 20

Townhouse in Citrus Ridge

5 out of 5 average rating, 4 reviews

Bright Modern Townhome Retreat

A renovated home is depicted, featuring light-colored exterior walls and a two-car garage with a white door. The landscaped front yard includes green grass and shrubs. A pathway of paver stones leads to the entrance, framed by decorative plants. Partly cloudy skies are observed above.

4.93 out of 5 average rating, 80 reviews

Disney - Sun - Fun

Kissimmee beach vacation rentals

A tranquil pool area is surrounded by lush greenery and palm trees. The water appears clear and inviting, with a rock formation creating a natural aesthetic. Lounge chairs are positioned around the pool, providing ample space for relaxation.

Apartment in Kissimmee

STar Island 1 Bedroom

4.96 out of 5 average rating, 121 reviews

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

A bright living area features large windows that allow natural light to fill the space. A comfortable sectional sofa is paired with a wooden coffee table. A wall-mounted smart HDTV is visible, and greenery is positioned beside the windows, enhancing the inviting ambiance.

Villa in Clermont

4.82 out of 5 average rating, 104 reviews

Family Friendly w/ KING bed, Resort Pool Sleeps 4

4.8 out of 5 average rating, 25 reviews

A two-story building features a yellow exterior with white railings and a distinctive cupola. Palm trees and lounge chairs are situated near the swimming pool, creating a tropical ambiance. A large blue umbrella provides shade in the outdoor area, contributing to a relaxed setting.

Condo in Citrus Ridge

Perfect Disney\Golf Vacation

5 out of 5 average rating, 43 reviews

Home in Clermont

Lakefront home - country - check for seasonal rate

4.96 out of 5 average rating, 196 reviews

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

Condo in Orlando

Your Family's Disney HQ~Sleeps 8~No Extra Fees!

4.92 out of 5 average rating, 26 reviews

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

Family friendly vacation rentals in Kissimmee

5 out of 5 average rating, 11 reviews

The Disney House • Immersive Rooms • Gaming Lounge

4.99 out of 5 average rating, 152 reviews

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Citrus Ridge

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

4.97 out of 5 average rating, 105 reviews

Magical Moments Luxury Disney Villa, Pool & Arcade

4.75 out of 5 average rating, 137 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

A vibrant game room is filled with Mario-themed arcade machines featuring colorful graphics and interactive screens. Brightly colored carpet adds a playful touch, while a basketball game and other activities occupy the space. The walls are adorned with mural artwork inspired by popular video games.

4.92 out of 5 average rating, 84 reviews

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

4.98 out of 5 average rating, 114 reviews

Dream Vacation | Sleeps 18 | Themed Arcade & Rooms

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.86 out of 5 average rating, 140 reviews

Resort Home 3.5 miles to Disney with home theater

A vibrant hallway showcases colorful murals featuring beloved characters, including Mickey Mouse and his friends, amidst playful scenes of amusement and adventure. The walls are painted with a blend of whimsical colors that add charm to the spacious area, complemented by a clean marble floor.