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Condo vacation rentals in Osceola County

Find and book unique condos on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Osceola County condo rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Guest favorite
The aerial view captures the inviting resort-style pool area surrounded by lush landscaping. Colorful canopies and seating areas enhance the outdoor space. Palm trees frame the scene, while the clubhouse is visible in the background, indicating a range of amenities available for guests.
Condo in Kissimmee
4.9 out of 5 average rating, 87 reviews

Coastal Retreat | 15 min to Disney

Top guest favorite
A modern living area is showcased, featuring a spacious sectional sofa with decorative pillows and a textured throw. A large smart TV rests on a light wood media console. Natural light floods through sliding glass doors, leading to a patio area with views of greenery and nearby attractions.
Condo in Kissimmee
5 out of 5 average rating, 13 reviews

Near Disney Magic!Free Parking!Free WI-FI!

Guest favorite
An exterior view of the apartment complex showcases a modern structure with beige walls and balconies framed by palm trees. The inviting pool area is visible from above, featuring lounge chairs and a beautifully landscaped space. Interior images present a spacious living area with a comfortable sofa, a dining area with blue chairs, and a serene bedroom with a king bed complemented by soft, light-colored bedding.
Condo in Kissimmee
4.9 out of 5 average rating, 68 reviews

304 Luxurious 2 Bd Close to Disney Storey Lake

Guest favorite
The living room features two comfortable chairs with playful decor, facing a large television displaying a Disney-themed image. A coffee table sits in the center, with a soothing area rug underneath. Sliding glass doors lead to a screened balcony, enhancing natural light in the space.
Condo in Kissimmee
4.88 out of 5 average rating, 69 reviews

Luxury 2BDR Disney Villa – Pool & Hot Tub

Guest favorite
A spacious wrap-around balcony is furnished with comfortable seating, featuring patterned cushions. Lush greenery and palm trees are visible, along with a view of the driveway and surrounding community. The clear blue sky highlights the serene ambiance of the outdoor space.
Condo in Osceola County
4.91 out of 5 average rating, 22 reviews

Vacay Villa

Guest favorite
Condo in Kissimmee
5 out of 5 average rating, 5 reviews

Tuscana Resort Cozy 2BR Condo + Resort Amenities

Guest favorite
A modern living area features a chic futon couch adorned with decorative pillows. A round marble coffee table is positioned at its center, accompanied by a small side table with a lamp. A vibrant pink throw blanket drapes over a comfortable chair, with greenery adding a touch of nature.
Condo in Kissimmee
4.9 out of 5 average rating, 60 reviews

Newly Renovated Condo near Disney & Universal

Top guest favorite
The exterior of a resort-style building is captured, featuring a multi-color facade with green and blue accents. Palm trees surround the entrance, and a clearly marked parking area is visible. The sky appears overcast, suggesting a calm atmosphere.
Condo in Kissimmee
5 out of 5 average rating, 14 reviews

La Brezza *New* Modern resort condo

Pet-friendly condo rentals

Top guest favorite
The living room features a spacious sectional sofa and a flat-screen TV mounted on a wooden console. Large glass doors provide a view of the patio and golf course, while natural light fills the room through the sheer curtains. A potted plant adds a touch of greenery.
Condo in Kissimmee
4.94 out of 5 average rating, 126 reviews

3 Bedroom w/large patio on Resort Golf Course

Superhost
A spacious bedroom features a plush, tufted headboard and a large window allowing natural light to fill the room. Two bedside lamps provide additional illumination, while modern furnishings add contemporary flair. A round mirror is mounted above the bed, reflecting the inviting ambiance.
Condo in Davenport
4.79 out of 5 average rating, 241 reviews

Brand New AwardWinning Renovated Condo Near Disney

Guest favorite
A designated pet area is shown, featuring two stainless steel bowls placed on a wooden stand beside a soft dog bed. The floor is finished in a light wood tone, enhancing the area’s functionality for pet owners.
Condo in Celebration
4.91 out of 5 average rating, 117 reviews

Pet Friendly in Orlando Area near Disney.

Guest favorite
The exterior of the condo presents a welcoming appearance with light yellow siding and a distinctive arch window. A well-maintained pathway leads to the entrance, bordered by manicured landscaping. Trees from the conservation area provide a natural backdrop, enhancing the serene environment.
Condo in Kissimmee
4.92 out of 5 average rating, 133 reviews

Cozy single story condo near Disney

Guest favorite
A spacious living area features large windows allowing natural light and views of green trees outside. A sectional sofa in a neutral tone is complemented by decorative blue cushions. A glass coffee table rests on a textured area rug, and a television is positioned on a low media console.
Condo in Kissimmee
4.89 out of 5 average rating, 113 reviews

Home away from home for the Parks!

Superhost
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.
Condo in Kissimmee
4.81 out of 5 average rating, 216 reviews

Family Friendly I Mins from Disney I Resort Pool

Top guest favorite
Condo in Kissimmee
4.99 out of 5 average rating, 110 reviews

Bongo’s Pad~ Gated Resort~ 3 Miles to Disney!

Superhost
The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.
Condo in Kissimmee
4.85 out of 5 average rating, 116 reviews

Westgate Vacation Villas - 1 Bedroom

Condo rentals with a pool

Guest favorite
The outdoor pool area is surrounded by palm trees and lounge chairs. Families are enjoying the water, while a spacious recreation building is visible in the background. Clear blue skies enhance the relaxing atmosphere of the resort.
Condo in Kissimmee
4.91 out of 5 average rating, 165 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Guest favorite
Condo in Kissimmee
4.85 out of 5 average rating, 92 reviews

*NEW*• Modern Luxury Condo

Guest favorite
A vibrant water park is featured with colorful slides and play structures, alongside a themed children's bedroom showcasing character decals. The king-sized bed is complemented by a bunk bed set. A stylish logo for Windsor Hills Resort emphasizes safety and fun.
Condo in Kissimmee
4.93 out of 5 average rating, 214 reviews

Andy's Toy Chest at Windsor Hills, Next to Disney!

Guest favorite
Condo in Kissimmee
4.92 out of 5 average rating, 93 reviews

Spacious 3BD Storey Lake Resort, Close to Disney

Top guest favorite
Condo in Kissimmee
4.96 out of 5 average rating, 140 reviews

Disney Oasis

Guest favorite
A bright bedroom is highlighted by two large windows with sheer gray curtains, allowing natural light to fill the space. A plush queen-sized bed with a tufted blue headboard is positioned against the wall. A bedside table with a lamp is placed next to the bed.
Condo in Kissimmee
4.89 out of 5 average rating, 27 reviews

Carri-Vision Suite, (Theme-Parks)Orlando/Kissimmee

Guest favorite
A sparkling pool is framed by lush palm trees and lounge chairs, inviting guests to relax. The cheerful two-story building in the background features vibrant blue-green accents and large windows, complementing the clear sky above.
Condo in Kissimmee
4.92 out of 5 average rating, 97 reviews

Modern, spacious, and relaxing!

Top guest favorite
A comfortable living area features a spacious gray sectional couch paired with an ottoman, creating a welcoming seating arrangement. Two framed artworks adorn the walls, while a red tray with snacks is placed on the ottoman. The open layout connects to a modern kitchen area with bar seating.
Condo in Kissimmee
4.97 out of 5 average rating, 69 reviews

*Pristine* Condo minutes from Disney & more!

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