Vacation rentals in Kissimmee

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

4.86 out of 5 average rating, 198 reviews

Near Disney Gated LakeView Pvt Heated Pool

LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

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.

4.94 out of 5 average rating, 123 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.

A vibrant outdoor area features a sparkling saltwater pool with fountain jets and colorful LED lighting. A large screen displays a movie, surrounded by lounge chairs. The area is enhanced by string lights and a cozy seating arrangement, creating an inviting space for relaxation and entertainment.

4.87 out of 5 average rating, 242 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

A large wooden dining table is surrounded by eight wooden chairs, set against a backdrop of stone-like walls with arched windows. A metal chandelier hangs overhead, while a decorative knight statue stands in the corner, adding character to the atmospheric space.

4.87 out of 5 average rating, 572 reviews

Magical 5-Bedroom Villa Near Universal's Wizarding

Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

Home in Buenaventura Lakes

The exterior of the house is displayed, featuring a well-maintained lawn with manicured shrubs and a palm tree. The light-colored structure is complemented by large windows, and decorative stones are arranged artistically in the landscape. A clear blue sky enhances the inviting appearance.

4.95 out of 5 average rating, 111 reviews

Your All in One Home, 17 mins from Disney World

Welcome to JeremyAnthonyHouse, a place that was created with so much love and care thinking of you. The house has everything you might need during your stay, it does not matter if it is for one night or an entire month; from bathroom amenities, free Netflix, Wifi, YouTube, in house laundry and dryer to kids' toys, security system. In addition, it has a private pool, easy access to expressways and theme parks. Very close to Disney springs and The Medieval Times Castle is a must see.

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.

4.93 out of 5 average rating, 104 reviews

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 screened lanai features a refreshing swimming pool, offering views of a quietly flowing pond surrounded by lush greenery. The space is illuminated by natural light filtering through the mesh enclosure, inviting relaxation amid nature.

4.82 out of 5 average rating, 121 reviews

Renovated pond view home + pool & outdoor theatre!

Enjoy the elegance of this peaceful and centrally-located place just minutes away from Disney World, Sea World, Universal Studios & all other fun attractions of Florida. The house is tucked away in the tranquil zone next to a beautiful quiet pond that you can enjoy every evening after a busy day playing. Enjoy the pool with the sun all day and a private outdoor home theatre at night. We have a grill for your full enjoyment too. Just an hour away from sandy beaches.

4.82 out of 5 average rating, 468 reviews

An outdoor swimming pool is framed by tropical palm trees, with a sun-drenched deck featuring lounge chairs and blue umbrellas. The pool area is surrounded by the hotel building, showcasing a casual and inviting atmosphere for relaxation.

Apartment in Kissimmee

Spacious 2BR Apt in Resort 10 min from Disney

Featuring comfortable, family-friendly amenities, this property provides relaxation in a peaceful, wooded setting while being close to all the major area theme parks. Enjoy the outdoor swimming pool or stay active at the fitness center and tennis courts. Families will appreciate the playground and children's pool. Additional conveniences such as a bar, free Wi-Fi, and free parking ensure this property is your home away from home near Orlando's famous theme parks.

4.86 out of 5 average rating, 102 reviews

Townhouse in Kissimmee

Disney Area| Private Pool| Resort Waterpark 2956

Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.

4.91 out of 5 average rating, 105 reviews

4BR Pool Home 4mi to Disney – Perfect for Families

Lindfields Private Pool Villa – Minutes from Disney Welcome to our charming Regal Villa, just 3–4 miles from Walt Disney World in the friendly Lindfields community. With sidewalks and mature landscaping, it’s a great place for evening strolls or relaxing after a day at the parks. Nestled in a quiet neighborhood, this 2,207 sq. ft. villa combines comfort and convenience, making it the perfect home base for your family getaway.

A spacious living area features a modern sectional sofa and two blue lounge chairs. A large flat-screen television displays a fireplace design, creating a cozy focal point. Natural light fills the room through window coverings, and a potted plant adds a touch of greenery.

4.91 out of 5 average rating, 247 reviews

Cozy House with Private Pool. Kissimmee/Orlando

Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.

Home in Buenaventura Lakes

5 out of 5 average rating, 37 reviews

Comfy Home with Hot Tub at Kissimmee/Orlando area

✨ Stylish and family-friendly retreat in a great Kissimmee location! Enjoy a comfy stay with a relaxing hot tub for up to 6 people and a fully equipped kitchen, perfect for creating meals together. Designed for comfort and convenience, ideal for your Orlando and Kissimmee vacation. IMPORTANT INFORMATION: 🚫 Parties or events are not allowed on the property or surrounding area. 🚭 No smoking.

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

23 locals recommend

Walmart Supercenter

979 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, 8 reviews

Condo in Kissimmee

New! Seven Eagles Hideaway at Reunion Resort

4.86 out of 5 average rating, 100 reviews

4m Disney Sun, Free Snacks, Golf, Pool• Spa• Games

4.91 out of 5 average rating, 33 reviews

Home in Clermont

10BR Theater Pool Little Mermaid Alice 16295

A private pool area features a crystal-clear pool, complemented by a spa and surrounded by paving stones. Lush palm trees are visible on the sides, and views of the golf course stretch in the background, creating a serene atmosphere for relaxation.

4.88 out of 5 average rating, 81 reviews

Luxury 4 Bedroom Home - Resort Access! Disney!

4.86 out of 5 average rating, 108 reviews

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

5 out of 5 average rating, 5 reviews

Home in Davenport

6 Bd/ 4.5 Ba Sleeps 15! Windsor Island (1677 KL)

A spacious entryway features a stylish staircase with wooden steps and a glass railing. A large Christmas tree decorated in soft colors stands next to a modern living area displaying a cozy sofa and contemporary artwork. A fireplace adds warmth to the ambiance.

4.87 out of 5 average rating, 68 reviews

The Eights House by Disney. Themed Island Dream

4.94 out of 5 average rating, 70 reviews

A light-filled living area is highlighted by a ceiling fan and a wall-mounted television displaying ESPN+. Two armchairs in a neutral tone and a sleek coffee table are positioned around a comfortable sofa, while large sliding doors open to a spacious balcony.

Apartment in Kissimmee

Cozy Condo Only 6 Minutes From Disney World

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 Davenport

Perfect Disney\Golf Vacation

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

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

A spacious living area features a comfortable brown couch and armchair, arranged around a coffee table. A ceiling fan hangs above, and a large flat-screen TV is mounted on the wall. Natural light enters through sliding glass doors, which lead to an outdoor space.

Condo in Davenport

4.62 out of 5 average rating, 39 reviews

Cozy Condo 15 minutes away from Walt Disney

4.79 out of 5 average rating, 14 reviews

An expansive outdoor pool area features palm trees, sandy beach volleyball courts, and thatched umbrellas. Lounge chairs in blue and white are arranged around the pool, creating a vibrant atmosphere. The lush greenery of the surrounding landscape adds natural beauty to the setting.

Home in Davenport

Beach Resort with pool tiki bar near Disney World

Family friendly vacation rentals in Kissimmee

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.

4.99 out of 5 average rating, 153 reviews

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

5 out of 5 average rating, 7 reviews

Home in Four Corners

ChampionsGate Home: Game Room, Pool Near Disney

5 out of 5 average rating, 3 reviews

4BR Disney & Universal Themed Villa Reunion Resort

5 out of 5 average rating, 14 reviews

Luxury House

4.92 out of 5 average rating, 84 reviews

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.

Home in Davenport

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

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.

4.87 out of 5 average rating, 141 reviews

Resort Home 3.5 miles to Disney with home theater

An inviting game room filled with arcade machines and a billiard table is showcased. The outdoor image features a resort-style pool with lounging areas surrounded by palm trees. The indoor spaces highlight themed bedrooms, with designer décor and playful character accents, ideal for family fun.

4.96 out of 5 average rating, 182 reviews

DISNEY 🦜, heated pool, themed, arcade, spa, BBQ

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.