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Condo vacation rentals in Winter Park

Find and book unique condos on Airbnb

Top-rated condo rentals in Winter Park

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Top guest favorite
Condo in Orlando
4.98 out of 5 average rating, 135 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.

Top guest favorite
A dining area on a spacious terrace features a wrought-iron table with seating for six. The table is set with plates, glasses, and utensils, accompanied by a bottle of sparkling wine. A large umbrella provides shade, with distant views of nearby buildings.
Condo in Orlando
4.87 out of 5 average rating, 320 reviews

🕶Your Private Terrace In The Sky🕶 Great Views

Great location for Universal Studios and EPIC, the Convention Center and amazing restaurants. This beautiful 2/2 apartment isone of the nicest at The Enclave Hotel & Suites. Relax on your own spacious private terrace while enjoying 270° views over Universal Studios, International Drive and the Orlando Eye. Newly renovated with Granite and travertine throughout. Stainless steel appliances and oversized smart TVs. Hotel amenities include indoor and outdoor pools, tennis, food court, pub and gym.

Guest favorite
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.
Condo in Citrus Ridge
4.86 out of 5 average rating, 135 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!

Top guest favorite
The living room features a cozy seating arrangement with a gray sofa and armchair, complemented by decorative pillows. A round table is positioned between the seats, and a large window offers views of Lake Bryan. Natural light brightens the space, enhancing the serene ambiance.
Condo in Orlando
4.88 out of 5 average rating, 265 reviews

Airbnb's Choice- Best at Blue Heron- Stunning View

"Airbnb's Choice" - When it was time for Airbnb to select a home to feature in their Instagram ad campaign, of the hundreds of homes in the Orlando area, they selected this one. "Shouldn't it be your choice as well?" Tastefully and professionally decorated - This is a spacious one-bedroom, two-bath lakefront condominium located at the Blue Heron Beach Resort. It's conveniently located just two blocks off I-4 and just 1 mile from the entrance to Disney with breathtaking views of Lake Bryan.

Guest favorite
The living area is brightened by large windows offering views over the lake. A comfortable sofa and seating area complement a dining table set for six. A television is positioned adjacent to a ceiling fan, creating a welcoming space for relaxation and dining.
Condo in Orlando
4.95 out of 5 average rating, 220 reviews

Bird’s-Eye View! 2bd/2 King/2Bath Disney Area

2 KING/ 2 BATH/ 2 BALCONY condo for an ideal getaway. Condo located within 10 min. from Disney, 15 min. for Universal, 25 min. to Downtown Orlando, and 1 hr to the beach. From the 12th floor unit, you can enjoy the sunrise over Lake Bryan in the morning and sunset - book the extra day, you’re gonna wish you did. Yep, that's right - your view is SKY HIGH, the best in Central Florida. Unit is fully equipped and very luxurious. Parking included in price and there are NO ADDITIONAL RESORT FEES.

Top guest favorite
A spacious living area features a large sectional sofa adorned with decorative pillows, positioned opposite a flat-screen TV on a modern console. Natural light enters through large windows, highlighting the open kitchen with wooden cabinetry and dining space. Decorative artwork adds a touch of color to the neutral walls.
Condo in Orlando
4.95 out of 5 average rating, 100 reviews

Renovated Condo 2 miles away from Disney Pool view

Welcome to our Orlando getaway! We’re Patricia and Fahem, esteemed Super hosts committed to curating an exceptional stay for our guests. Nestled in the heart of Orlando our condo offers comfort, style, and easy access to an array of family-friendly attractions. Our space is designed to cater to families, couples, or solo adventurers eager to explore the diverse attractions Orlando has to offer. Beyond the magic of Disney, discover a world of excitement at other nearby family-friendly spots.

Guest favorite
A cozy living area features a spacious gray sofa positioned in front of a large window, allowing natural light to fill the room. A decorative vase of vibrant flowers is placed on a dark dining table. A wall adorned with imagery adds character to the space.
Condo in Orlando
4.82 out of 5 average rating, 468 reviews

Amaranta/Studio beautiful balcony LAKE VIEW 🫶❤️

Beautiful Studio 8m. Universal/Epic. 1 queen bed, 1 XL sofa bed, in the living. You can enjoy a wonderful lake view!! Free parking, 2 outside pool and 1 heated inside pool. The Studio have in the kitchen: Top stove with two burners, refrigerator, microwave oven, coffee maker, toaster, blender, pots, plates and silverware, for your convenience. In the bathroom. A nice jacuzzi!! The laundry is two doors away from the Studio. Under cost. This Studio not accept children, baby’s or pets.

Guest favorite
A spacious living area features a comfortable sofa and two turquoise chairs, inviting relaxation. A large rug with geometric patterns anchors the space, while a modern art piece adds a colorful focal point. Natural light floods in through large windows, highlighting the open layout.
Condo in South Eola
4.96 out of 5 average rating, 165 reviews

Downtown Condo w/ Treetop Views & Free EV Charging

Rooftop Deck with Skyline Views - Free Downtown Parking - Free EV Charging - Fast WiFi Lots to love about this condo! We are just four blocks from Lake Eola. Plenty of great restaurants and nightlife options close, yet we are just far enough from the noise and traffic of downtown to enjoy some quiet too. Walk to Grocery Store (Publix), Fine Dining, Bars, Clubs, Performing Arts Center, Lake Eola Farmer's Market, Kia Center Concerts and Sporting Events and more!!!

Guest favorite
A modern living area features a large sectional sofa and a glass coffee table. Natural light floods the space through multiple windows, enhancing the warm wooden flooring. A round dining table is set for four, while a decorative artwork piece adorns the wall.
Condo in South Eola
4.86 out of 5 average rating, 169 reviews

Beautiful Downtown Condo 1/1

This fully furnished 1/1 apartment, comes fully equipped with all the necessities you need for your vacation or short stay to Orlando, The City Beautiful. We have fully remodeled our house and would like to share the experience with you. The bedroom come with California king bed. Our kitchen has pots, pans, plates and silverware, as well as a Nespresso coffee machine for your morning wake up! We have our laundry machines in-house and yes, you can use them.

Guest favorite
A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.
Condo in Winter Park
4.84 out of 5 average rating, 114 reviews

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

Guest favorite
A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.
Condo in Kissimmee
4.9 out of 5 average rating, 186 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

Superhost
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.
Condo in Orlando
4.9 out of 5 average rating, 506 reviews

Westgate Palace Resort 2 bedroom

Offering a 2 Bedroom apartment at Westgate Palace with queen bed, twin beds and kitchen. Near Universal Studios® for an unforgettable vacation onsite dining options a variety of activities, splash about in the coral reef pool. Just off International Drive and within minutes of area attractions. Sleeps 4 A great location to visit the local attractions.

Popular amenities for Winter Park condo rentals

Quick stats about condo rentals in Winter Park

  • Total vacation rentals

    Explore 10 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Winter Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Park rentals

  • 4.9 Average rating

    Winter Park stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Winter Park's top spots, include Orlando Science Center, Harry P. Leu Gardens, and Orlando Museum of Art

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