Vacation rentals in Kissimmee

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

Bring the whole family to this great home with lots of room for fun. You will love our Peter Pan- themed bedroom; custom Mario-themed game room with commercial quality games, private pool and spa with a great outdoor dining area. Only a short walk to the resort pools, lazy river, restaurant, Tiki bar and much more. Located just 15 minutes from Disney World and 30 Minutes from Both Universal and Sea World, Close enough to the attractions to get there quickly, far enough away to enjoy family time.

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.

5 out of 5 average rating, 3 reviews

S3910 | Near Disney Home w/ Pool & Games

Enjoy your stay in this spacious and modern home near Disney. Featuring an open-concept design, fully equipped kitchen, cozy living and dining areas, and a large sliding door to the outdoor space. The private backyard offers a pool, spa, dining area, and outdoor shower. A game room adds extra fun. The home has six bedrooms, including three themed rooms (Mario Kart, Moana, and Disney) and three standard rooms. Perfect for families and groups seeking comfort and unforgettable memories.

A single-story home is presented with a light tan exterior and a welcoming front yard. Lush greenery surrounds the property, featuring neatly trimmed shrubs and palm trees. A paved driveway leads to a two-car garage with solar panels on the roof, providing an energy-efficient touch.

5 out of 5 average rating, 60 reviews

Family Vacay with Pool near WDW!

We hope to welcome you to this enchanting family retreat in Kissimmee, Florida, just 20 minutes from the magic of Walt Disney World Resort! This sunlit oasis is designed for unforgettable family vacations. Dive into your screened private pool, a cool oasis under the warm Florida sun, to create memories that'll last a lifetime. After an exhilarating day at the parks, return to this cozy home where you'll find the perfect blend of entertainment and relaxation.

A private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

4.91 out of 5 average rating, 255 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

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, 200 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.

The private pool area is surrounded by a screened enclosure, featuring a clear blue pool. A patio with dining furniture and a BBQ grill is visible, alongside lounging chairs. Two homes can be seen in the background, creating a spacious ambiance.

4.89 out of 5 average rating, 119 reviews

Retreat w/ Pvt Pool + Club Access | Disney 15min

Experience luxury in this spacious 5-bedroom, 5.5-bathroom home located just 15 minutes from Disney. Relax in elegant living areas with Smart TVs and an Xbox One, or step outside to your private pool with stylish patio furniture and BBQ grill. The open-concept kitchen and dining area are perfect for gathering, while the Windsor at Westside resort offers a lazy river, pools, fitness center, playgrounds, and sports courts, all just steps away.

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 Kissimmee

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 :)

An outdoor space features a screened-in pool area with a clear blue pool and spa. Comfortable lounge chairs are positioned beside the pool, with a dining table set beside them. Lush greenery is visible beyond the fenced yard, creating a private and relaxing environment.

4.79 out of 5 average rating, 132 reviews

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!

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.

5 out of 5 average rating, 7 reviews

9BR Retreat | Sleep 27 | Theater | Huge Pool & Spa

Welcome to your Storey Lake getaway! This spacious 9-bedroom home with a private pool, spa, and game room is designed for unforgettable family vacations—just minutes from Disney, dining, and top attractions. Relax, recharge, and make memories together.

5 out of 5 average rating, 4 reviews

NEW 07 Bedroom Themed Luxury in Solara Resort

* Accommodates: 16 * Bathrooms: 5 * Bedrooms: 07 * Property type: Luxury Villa * Location: Solara Resort

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

4.99 out of 5 average rating, 68 reviews

This themed bedroom features two full beds adorned with green and white bedding. Wall art depicts Mickey Mouse and Minnie Mouse, complemented by lush green foliage accents. Soft lighting enhances the cozy ambiance, and a plush carpet covers the floor.

Townhouse in Kissimmee

2588-Stunning Themed-House at Storey Lake

4.8 out of 5 average rating, 70 reviews

The screened pool area features a spacious swimming pool, illuminated in calming blue tones. A jetted tub is integrated into the pool area, surrounded by brick paving. Lounge chairs are positioned nearby for relaxation under the protective screen.

Villa in Davenport

Best Value BnB Disney Villa W/ Private Pool & SPA

4.85 out of 5 average rating, 48 reviews

Restful 4BR / 3BA with BBQ, Heated Pool & SPA.

5 out of 5 average rating, 5 reviews

Home in Four Corners

Disney World Epic Luxury Marvel Superhero Haven

An exterior view of a two-story home is presented, featuring a screened-in private pool and spa surrounded by a patio. Additional images showcase a game room with a pool table, vibrant wall art, and an inviting living space leading to the pool area.

4.88 out of 5 average rating, 85 reviews

* Top-Rated Villa - Sleeps 14 - Free Resort *

5 out of 5 average rating, 4 reviews

New! Epic Solara Playhouse | Custom Bunks + Slides

A private screened-in pool is surrounded by a clear enclosure, offering unobstructed views of a serene lake and lush greenery. Sunlight reflects off the water, enhancing the tranquil atmosphere. Comfortable lounge chairs are positioned nearby for relaxation.

4.92 out of 5 average rating, 61 reviews

Serene 4BR Pool Home Near Disney

5 out of 5 average rating, 19 reviews

Spacious Home | Near Disney | Perfect for families

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, 119 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

4.79 out of 5 average rating, 24 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

Condo in Orlando

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

A 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.

4.74 out of 5 average rating, 27 reviews

Exclusive 8BR Themed Villa • Private Pool Retreat

4.82 out of 5 average rating, 11 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

4.8 out of 5 average rating, 40 reviews

A screened-in porch overlooks a serene lake, featuring two light-colored chairs and a round table. Lush greenery surrounds the area, and distant buildings are visible across the water. The porch is partially shaded, inviting relaxation with a view of the outdoors.

Apartment in Davenport

Lake view 912

Family friendly vacation rentals in Kissimmee

A collage of vibrant and themed recreational rooms showcases a game room with a Star Wars mural, a pool table, and unique lighting. The outdoor area features a large resort-style pool surrounded by palm trees and lounge chairs, complemented by a private spa.

5 out of 5 average rating, 36 reviews

Updated Vacation Home Solara by Disney w/Pool

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, 150 reviews

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

4.92 out of 5 average rating, 132 reviews

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

A bright pool area is surrounded by a screened enclosure that offers protection from insects. A clear blue pool is visible, accompanied by six chaise lounge chairs positioned nearby. Warm yellow walls frame the space, enhancing the tropical feel of the private outdoor oasis.

4.93 out of 5 average rating, 341 reviews

*Disney Home* Heated Priv Pool/Spa 7beds, Arcade!

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

4.86 out of 5 average rating, 436 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

5 out of 5 average rating, 8 reviews

Condo in Kissimmee

Toy Story Magic Studio Close to Disney

4.78 out of 5 average rating, 316 reviews

Townhouse in Kissimmee

Fantasy World 2br, Luxury on Wet n Wild #4

An air-conditioned game room features vibrant murals of superhero characters on dark blue walls, accented by glowing designs. An air hockey table and a multi-game arcade machine are visible, providing entertainment options for guests of all ages.