Condo holiday rentals in Kissimmee

4.91 out of 5 average rating, 254 reviews

Disney Oasis by the lake

Discover our charming condo near Disney, nestled in a resort-style community. Enjoy complimentary parking and No resort fees!The beautiful clubhouse offers a game room, gathering areas, and a fitness center. Unwind by the serene heated pool or take advantage of the second pool. Engage in activities at the golf cage, tennis, basketball, and volleyball courts, or let kids play at the playground. Stroll along scenic walking trails that wind through landscaped areas and ponds for a tranquil retreat.

4.98 out of 5 average rating, 133 reviews

Private Rooftop Suite! No resort fees!

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

The modern living area features a spacious gray sectional sofa accented by colorful cushions. A minimalist coffee table is positioned centrally, and large sliding glass doors provide a view of the outdoor space, allowing natural light to fill the room. Light-colored cabinetry and appliances are visible in the kitchen area.

4.93 out of 5 average rating, 228 reviews

3150-303 Condo Resort Water Park Pools near Disney

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

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, 145 reviews

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Welcome to the Adventureland bungalow! This 2 bd/ 2 ba stay features a Tiki room living room with a sofa bed. The upgraded kitchen and bamboo bar are perfect to kick back and relax, or enjoy the screened in patio with tiki torches and seating area. The Jungle Cruise master bedroom features a king size bed and lovely waterfront views with lush greenery. The Pirate bedroom is fit for a captain (or two!) and has two twin xl beds. Air conditioning throughout. Located on the third floor/stair access.

4.92 out of 5 average rating, 106 reviews

Resort Style Sunshine Oasis near Theme Parks

Discover Orlando's charm at our resort-style oasis in a gated community with lots of amenities! Nestled near Disney, this modern haven features 2 stunning pools for ultimate relaxation. Delight in nearby restaurants, perfect for foodies. Families will love the kid-friendly atmosphere, and fitness enthusiasts can stay active in the on-site gym. Our clean, contemporary design ensures a comfortable stay, making it an ideal choice for your Orlando getaway. Conveniently located on the first floor.

4.86 out of 5 average rating, 133 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!

4.89 out of 5 average rating, 119 reviews

An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.

Condo in Osceola County

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

4.95 out of 5 average rating, 150 reviews

The exterior of a modern two-story building is shown, featuring a combination of light grey and white siding. Lush palm trees frame the front, with a paved driveway visible. A parked vehicle is positioned in front of the entrance, and a sunny blue sky is above.

Condo in Champions Gate

Spacious Condo for 8 Golf Waterpark 15 min Disney

Welcome to your Orlando family getaway! This 3-BR condo at Champions Gate offers a direct Golf Course view and sleeps up to 4 adults and four kids. Two rooms feature King beds, and one has two Full beds. Just 15 mins from Disney Parks! Enjoy complimentary access to the fabulous Oasis Club (3 pools, gym, Tiki Bar) and the Retreat Club. Full kitchen access saves you money. Champions Gate also boasts a 36-hole Greg Norman championship golf course! Location & luxury for all ages.

A modern living space features a gray sectional sofa adorned with blue accent pillows, positioned near a glass coffee table. Light fills the room through large windows, highlighting the open layout that connects to a dining area with elegant furnishings and a kitchen visible in the background.

4.9 out of 5 average rating, 184 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

The image showcases a colorful resort with pastel-colored buildings reflecting on a calm lake. Lush greenery surrounds the area, enhancing the tranquil setting. A clear blue sky is visible, with a playful Mickey Mouse graphic indicating proximity to Disney World.

4.98 out of 5 average rating, 299 reviews

Amazing ❤️ Water View Condo near Disney & Universal

Welcome to Runaway Beach Club — your peaceful escape just minutes from the magic! With airy high ceilings and Key West-style decor, you’ll feel at home the moment you walk in. Whether you’re visiting theme parks or just want to relax, this cozy retreat is tucked away from the chaos but close to everything. Perfect for couples, small families, or business travelers. Book your stay and unwind in your own private slice of paradise!

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.

4.93 out of 5 average rating, 122 reviews

Modern, spacious, and relaxing!

This stylish place to stay is perfect for group trips, from 1 day to a week stay, or a long stay. Very large patio for outside dining, open space living room, kitchen, and dining. Spacious master bedroom and bathroom. Spacious 2nd bedroom and bathrooms. Everything you'll need for you fine dining, or mac & cheese. Car seat, booster seat, and stroller available. Washer and dryer and iron available,

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.

4.88 out of 5 average rating, 233 reviews

Westgate Vacation Villas - 1 Bedroom

Offering a 1 Bedroom apartment at Westgate Vacation Villas with King Bed, Sofa Bed and full Kitchen Westgate Vacation Villas comforts of a furnished only home 1 mile from Disney and close to the other Orlando attractions, restaurants and shopping. with studios - 2 bedr'm suites+variety of amenities 14 heated pools + award-winning Drafts Sports Bar & Grill

Popular amenities for Kissimmee condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.84 out of 5 average rating, 161 reviews

Contemporary apartment near Disney with WIFI

A spacious infinity pool is surrounded by palm trees and lush greenery. The pool area includes a child-friendly section and is bordered by vibrant landscaping. The hotel buildings are visible in the background, providing a resort-like atmosphere.

4.92 out of 5 average rating, 128 reviews

Pet friendly Orlando area near ESPN Center

4.93 out of 5 average rating, 132 reviews

Disney Dream Condo & Pool

4.83 out of 5 average rating, 94 reviews

Newly Remodeled 2-bedroom 15 minutes to the parks.

An aerial view captures a large swimming pool curving gracefully, surrounded by palm trees and lounge chairs. Adjacent to the pool, a kiddie pool is visible. The tranquil waters of Lake Bryan glimmer in the background, bordered by lush greenery.

4.94 out of 5 average rating, 124 reviews

Modern Lake view Condo 1 mile from Disney

4.98 out of 5 average rating, 236 reviews

Modern Apartment with lake view Close to Disney

4.93 out of 5 average rating, 41 reviews

Condo in Four Corners

2BD Champions Gate Magical Near Disney (CG 1177)

A stunning water park showcases multiple pools and attractions surrounded by palm trees. The lazy river winds through the landscape, while vibrant water slides stand ready for enjoyment. Ample lounging space is offered for relaxation, highlighting the inviting atmosphere of this recreational area.

4.77 out of 5 average rating, 31 reviews

Stunning 3BR Condo Near Disney

Pet-friendly condo rentals

4.85 out of 5 average rating, 292 reviews

An aerial view of a resort pool area showcases a winding pool surrounded by lush palm trees and tropical landscaping. Lounge chairs are arranged along the poolside, with shaded cabanas nearby. The resort features a terracotta roof and is set against a backdrop of greenery.

Condo in Champions Gate

Magical Champions Gate 3/2 Tuscan Penthouse

The living room features large sliding glass doors that open to the balcony, providing a view of the lake. A contemporary electric fireplace sits beneath a 65-inch smart TV. Comfortable seating includes a sofa, an armchair, and a coffee table, with warm curtains adding a touch of color.

4.96 out of 5 average rating, 106 reviews

Penthouse Lakeview Minutes to Disney/ Universal

A well-maintained exterior of a two-story condo is displayed, featuring a combination of yellow siding and red brick accents. Large windows allow for ample natural light, while neatly trimmed hedges line the walkway leading to the entrance, creating an inviting and accessible entry point.

4.78 out of 5 average rating, 113 reviews

Waterview Condo Close to Disney

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.

4.94 out of 5 average rating, 141 reviews

3 Bedroom w/large patio on Resort Golf Course

A spacious living area features comfortable seating with gray sofas and decorative pillows. A coffee table sits at the center, accompanied by a decorative lamp. The open-concept design leads to a modern kitchen with wooden cabinetry, visible in the background.

4.81 out of 5 average rating, 129 reviews

Beautiful Lake View Condo, Vista Cay-1004

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.

4.79 out of 5 average rating, 256 reviews

Brand New AwardWinning Renovated Condo Near Disney

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.

4.92 out of 5 average rating, 150 reviews

Cozy single story condo near Disney

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.

4.9 out of 5 average rating, 130 reviews

Home away from home for the Parks!

Condo rentals with a pool

4.75 out of 5 average rating, 4 reviews

Mickey's Dream * Themed Game Area 2 BR

4.91 out of 5 average rating, 32 reviews

*NEW* Secret Resort | Kissimmee Lakeview Condo

5 out of 5 average rating, 13 reviews

Magic Spring

An outdoor patio is visible, featuring a metal dining set with a rectangular table and four chairs. A small potted plant is centered on the table. The background includes a serene waterfront view with blue skies and greenery.

4.73 out of 5 average rating, 105 reviews

New -Bright & Charming Waterfront Condo

The illuminated pool area features clear blue water reflecting the vibrant colors of dusk. Surrounding palm trees create a tropical ambiance, while lounge chairs are arranged nearby. The serene waterfront view highlights the transitioning sky, offering a peaceful retreat at twilight.

4.95 out of 5 average rating, 43 reviews

Stunning waterfront Views 1 mile to Disney 2 bath

4.93 out of 5 average rating, 14 reviews

Cozy condo in waterpark resorts and golf course

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.

4.97 out of 5 average rating, 75 reviews

*Pristine* Condo minutes from Disney & more!

A spacious bedroom features a large bed with white linens, complemented by bedside tables with lamps. A ceiling fan is mounted above, and large windows with elegant curtains allow natural light to illuminate the room. A decorative globe and a bench provide additional accents.