Condo vacation rentals in Kissimmee

4.91 out of 5 average rating, 171 reviews

Chic Disney Resort Condo • Pool Access Near Parks

Magical Disney getaway that sleeps up to 6 guests just 7 miles from Disney. Enjoy full resort perks & amenities, fast free Wi-Fi, and year-round pool & hot-tub access. • Enjoy a heated pool, hot tub, game room, and fitness center, and Smart TVs • Full kitchen and cookware • Free parking steps from elevator • Located in a secure, gated community Perfect for families, couples, or business travelers. Near Universal, SeaWorld & top dining! Relax on a balcony & reach every park in under 15min!🏰✨

4.85 out of 5 average rating, 171 reviews

A resort-style pool area is surrounded by palm trees and lush landscaping, with inviting lounge chairs arranged nearby. The clear water reflects a bright sky, and a separate lounge area with a decorative façade is partially visible in the background.

Condo in Davenport

Orlando Spacious 2 Suites & Resort-Style Pool

Freshly renovated condo featuring TWO SPACIOUS PRIVATE SUITES, each with its own full bathroom — ideal for families, couples, and business stays. Located in ChampionsGate, 19 minutes from Disney and 30 minutes from Epic Universe and Universal Parks. Only 4 minutes from the Omni Orlando Resort at ChampionsGate, popular for golf, conferences, and special events. Enjoy full access to Tuscana Resort amenities at no extra cost, including a heated pool with conservation views and a relaxing hot tub.

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.87 out of 5 average rating, 142 reviews

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

The open living area is furnished with a comfortable sofa and a modern coffee table, complemented by a large flat-screen TV mounted on the wall. Natural light flows in through glass doors, leading to a balcony. A serene color palette and light wood flooring create a welcoming environment.

4.87 out of 5 average rating, 119 reviews

3176-301 Resort 2BR Apt by Disney World Orlando

Just minutes from DISNEY WORLD ORLANDO FLORIDA, fully renovated 2bed/2bath & fully equipped apartment for up to 6 guests, located in the family friendly Secret Lake Resort. Master suite has a KING bed & 65" Smart TV. Second bedroom has 2 Full beds and a 40" Smart TV. The open floor plan blends Kitchen, Dining and Living room with a 70" Smart TV. Close to Parks, Margarita Ville Water Park, Outlet malls & Retail stores. All amenities included: Wi-Fi, Pool, Gym & BBQ area. NO RESORT FEES

A winding lazy river pool is surrounded by lush palm trees and tropical landscaping. Water features, including slides and spraying elements, create an engaging atmosphere. Steps lead into the pool, which is framed by natural stone and tile, offering a serene escape in a vibrant setting.

4.98 out of 5 average rating, 171 reviews

Top Floor Condo Lake View near Disney Storey Lake

Experience Florida at its best in our beautiful condo! Enjoy breathtaking sunrises and sunsets from our private balcony or cook in our luxurious kitchen. Your kids will love their "Frozen" themed bedroom! We are perfectly located just minutes from Disney, Universal, SeaWorld, and Legoland. Stay in a luxury resort close to all the magic, with world-class amenities and two clubhouses. Whether it is a family trip or a relaxing getaway, our home is ready for you. We can’t wait to host you!

4.83 out of 5 average rating, 139 reviews

Cozy space 5/10 universal & epic

Take it easy at this unique oasis and tranquil getaway that is located in the heart of Orlando!! Want to have fun?! Literally walking distance from Universal Studios, Want to go shopping?! 5 mins from Millenia Mall and Premium Outlets. Want to experience Orlandos hottest nightlife or stroll through the city it’s 15 mins from Downtown , Do you want to meet Mickey Mouse or shamu?! 15 mins from Disney and sea-world. Even take a dip in the complex pool or play tennis!!

4.88 out of 5 average rating, 107 reviews

Condo in Davenport

A luxurious living just 15 min/Disney

Get ready for an exciting family adventure at our fabulous 2-bedroom condo in the breathtaking Tuscana Resort. Our unbeatable location places you at the center of all the action, whether you're eager to dive into the thrilling theme parks, tee off on a beautiful golf course, treat yourself to some fantastic shopping, or simply soak up the radiant Florida sun. This is the perfect spot for an unforgettable Orlando vacation—there's endless fun waiting for everyone!

A vibrant pool area is showcased, featuring bright water play structures including a pink water umbrella and colorful fountains. Sun loungers and umbrellas in various colors surround the pool, with palm trees lining the background under a clear blue sky filled with fluffy clouds.

4.87 out of 5 average rating, 433 reviews

Gated community, 5 miles from Disney

Decorated prioritizing comfort for our guests, smart lock for a self check in. Our community is now part of Calypso Cay Resorts. All of our guests are allowed to cross over to all 3 properties including the big Holiday Inn side. 5 swimming pools in total, 3 hot spas, water slides, mini golf, basketball, tennis, volleyball, playground, rock climbing, and more. They also have a bar/lounge, a snack bar/deli, coffee shop, 300 feet Zipline available for a purchase.

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

4.93 out of 5 average rating, 216 reviews

Magical Stay Near Disney & ESPN

🏰 Make magical memories just minutes from Disney & ESPN! Bright 3BR, 2BA condo for up to 6 guests in a safe, gated community—perfect for families or friends! Why you’ll love it: Family-friendly & ideal for kids 🏡 Relax in comfort after a fun day at the parks 🍳 Fully equipped kitchen for easy meals 🛍️ Close to restaurants, shopping & entertainment 🎢 Only 1.5 miles from Disney World & ESPN Stress-free, unforgettable family vacation awaits!

A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.

4.92 out of 5 average rating, 152 reviews

Modern Condo with Lake View Near Disney 3151

STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

An aerial view of the resort reveals a beautifully landscaped area with palm trees and pathways. The inviting outdoor pool is surrounded by lounge chairs, while nearby, a serene waterway meanders through the lush green landscape. The villas are nestled harmoniously among the greenery.

4.97 out of 5 average rating, 155 reviews

Marriott Sabal Palms 2BD Villa

Discover the magic of Orlando vacations. Welcome to a tranquil retreat in the heart of Orlando, the world's theme park capital. The resort's lush landscape offers a feeling of seclusion, while the expansive grounds provide an outdoor pool, shuffleboard court and life-size chess set. Choose from an array of activities, from poolside relaxation to theme park thrills, plus fabulous dining, shopping and golf just steps away from your villa.

A clear view of a pool surrounded by lounge chairs and palm trees, reflecting the sunlight. Umbrellas provide shade, and green lawns are visible in the background. The calm water enhances the serene environment, creating a relaxing outdoor space.

4.83 out of 5 average rating, 252 reviews

Family Friendly I Mins from Disney I Resort Pool

Welcome to your Disney dream getaway! Our inviting condo nestled in a secure and peaceful gated complex just a 20-minute drive from the parks, is your ultimate haven for a magical vacation. Ideal for families and friends, it comfortably accommodates up to 7 guests. Your stay unlocks access to two pools, hot tubs, a tennis court, gym, and BBQ areas for outdoor gatherings. Welcome to the start of your Disney adventure!

Popular amenities for Kissimmee condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.67 out of 5 average rating, 240 reviews

Cozy Condo near Disney and Parks

4.85 out of 5 average rating, 40 reviews

Cozivill

A spacious living area features two large sofas arranged around a circular coffee table. A modern television is mounted on a wall unit, displaying a scenic image. Natural light enters through sliding glass doors that lead to an outdoor space.

4.99 out of 5 average rating, 87 reviews

Renovated Luxury Condo in Windsor Hills Resort!

4.94 out of 5 average rating, 50 reviews

3BR Champions Gate Condo • Resort Access, Sleeps 9

A bright and airy studio is showcased with large windows allowing natural light to fill the space. A king-size bed with a patterned quilt is paired with a comfortable daybed. A 65" TV is mounted on the wall, and a small dining area features two chairs with a vase of flowers.

4.8 out of 5 average rating, 96 reviews

XLPatio Studio/KingBed/Universal

4.94 out of 5 average rating, 69 reviews

Condo in Four Corners

Guest favorite! Near Disney

A vibrant view of a famous castle set against a clear sky. Surrounding gardens feature manicured lawns and landscaped trees, with pathways leading to various areas. Guests and visitors are seen gathering in the open space, creating a lively atmosphere.

4.75 out of 5 average rating, 63 reviews

Apartment near Disney World. 2 bedrooms

A bright living area is shown with a modern grey sofa, elegant dining table set for four, and a smart TV. Large glass doors lead to a private balcony with palm trees visible outside, enhancing the spaciousness of the room.

4.92 out of 5 average rating, 90 reviews

Chic 2BR Condo w Balcony Near Epic Universe

Pet-friendly condo rentals

A spacious pool area is surrounded by palm trees and well-maintained landscaping. Lounge chairs are arranged around the swimming pool, with a modern clubhouse visible in the background. Sunny blue skies create a bright atmosphere over the inviting outdoor space.

4.93 out of 5 average rating, 150 reviews

Storey Lake Water Park Resort Condo next to Disney

A bright bedroom is presented, featuring a spacious bed with crisp white linens and a decorative orange pillow. Soft overhead lighting highlights the warm tones of the wooden headboard. The room includes an ensuite bathroom, visible through an open door, enhancing accessibility.

4.91 out of 5 average rating, 681 reviews

Westgate Palace Resort 2 bedroom

4.88 out of 5 average rating, 169 reviews

Vista Cay Luxury Prize, Next to EPIC and OCCC

4.88 out of 5 average rating, 181 reviews

Family Fun Condo: Free Water Park, Mins to Disney

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

4.92 out of 5 average rating, 156 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

A modern living area is showcased with a sectional sofa, lounge chairs, and a coffee table. Open shelving displays decorative items. The kitchen area is visible in the background, featuring pendant lighting and sleek appliances. Natural light enhances the neutral tones of the space.

4.93 out of 5 average rating, 163 reviews

Remodeled 2BR/2BA Near Disney, Pool +WiFi +Parking

The vibrant pool area is framed by tall palm trees and features a clear blue water surface. Loungers and umbrellas are positioned around the pool, with a fountain visible in the background, creating a relaxing outdoor space.

4.83 out of 5 average rating, 186 reviews

Disney Adorable Condo in the heart of it ALL! 1/1

4.75 out of 5 average rating, 139 reviews

Storey lake, The Cove.

Condo rentals with a pool

A bright, modern living area features a comfortable sofa adorned with decorative pillows. Natural light filters through the window, enhancing the open layout that seamlessly transitions to a well-equipped kitchen with a spacious island and three wooden stools.

4.94 out of 5 average rating, 54 reviews

1st floor By Pool, Kids Play area, Close to Disney

4.77 out of 5 average rating, 149 reviews

Themed Rooms & Lake Views: Your Kissimmee Escape!

An open living space features large glass doors leading to a balcony, offering lake views. A comfortable gray sofa is paired with two accent chairs, while a round coffee table sits on a colorful area rug. Soft natural light fills the room, enhanced by decorative plants.

4.82 out of 5 average rating, 93 reviews

Lake View | Pool View | King Bed | Bunk | 2 bath

A large stone sign displays the name 'Windsor Palms' surrounded by lush greenery and colorful flowerbeds. Palm trees are seen flanking the sign, under a clear blue sky, indicating an inviting entrance to the gated resort community.

4.91 out of 5 average rating, 158 reviews

Resort condo minutes from Disney!!!

An aerial view of the Reunion Resort landscape presents well-maintained golf courses alongside residential buildings. A large pool area is visible, surrounded by palm trees and lounge chairs. The horizon is marked by rolling greens and distant resort structures under a partly cloudy sky.

4.78 out of 5 average rating, 236 reviews

Retreat Golf View & Amazing Pools Near Disney

4.95 out of 5 average rating, 79 reviews

Elegant 3BR Condo Near Disney w/ Pool

5 out of 5 average rating, 25 reviews

Lake & Pool View 3BR Condo • Spacious Near Disney