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.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.

Condo in Orlando

4.98 out of 5 average rating, 186 reviews

Lakefront Resort Condo near Disney & Universal

Located minutes from Disney World and Universal Studios you are right in the middle of all the action with Disney Springs, Islands of Adventure,Sea World, Magic Kingdom,Epcot, two major outlet malls, and many other attractions .This resort style condo features a balcony overlooking beautiful Lake Bryan ,a beautiful pool that offers a full Tiki bar and food menu.Concierge services for Park tickets available. Free parking ,24hour security. Free HBO & Netflix .No deposit required and no extra fees.

Superhost

A light-filled seating area features two plush chairs with decorative pillows, positioned near a large window dressed in soft curtains. A potted plant adds a touch of greenery, while a stylish rug lays on the hardwood floor, enhancing the overall cozy ambiance.

Condo in Orlando

4.82 out of 5 average rating, 109 reviews

2/2 PENTHOUSE DOWNTOWN with large Billiard room

This fully renovated mid century beauty has all the necessities you will need for your long vacation or short stay in Orlando. The Penthouse has 2 bedrooms with king size beds, and two full bathrooms. The unit also has a large billiard room, with TV where all streaming services are available. Kitchen comes with oven, pots, plates.... and a Nespresso machine with free pods for your morning wake up. Washer/dryer are available. *we ask our guests to make inquiries before booking the apartment*

Superhost

A spacious living area is showcased with a comfortable gray sofa and a round coffee table placed on a light blue area rug. Modern wall art adorns the walls, and a dining table with four chairs is visible in the background. Natural light fills the space, highlighting the vaulted ceilings.

Condo in Ventura

4.83 out of 5 average rating, 117 reviews

Entire Condominium- Luxury Gated Community

Gorgeous, recently renovated 1 bedroom condominium with vaulted ceilings and tons of natural light. This condo has the exclusivity for a single guest or the intimacy for a couple. It is even spacious enough for a small family or group of friends with a Queen Bed and Twin Bed in the bedroom and a comfortable Queen Pull-out bed in the living room. This unit is located in the Heart of Orlando. 8 minutes from the Airport. 25 minutes from Universal. 30 minutes from Disney. 15 minutes from downtown!

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 Florida Center

4.86 out of 5 average rating, 289 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 spacious studio features a king-sized bed adorned with soft linens. A round dining table with stylish blue chairs is positioned nearby, alongside a vibrant decorative rug. Large windows provide natural light, framed by flowing gray curtains, while a modern chandelier hangs above, enhancing the elegant decor.

Condo in Florida Center

4.88 out of 5 average rating, 232 reviews

Maria Luz Studio-Huge Terrace/Universal area.

We are sure that you will fall in love with our STUDIO!! Beautiful, Romantic and incredible lake view Studio!! King side bed and sofabed. Enjoy a LARGE PRIVATE TERRACE. Enjoy the jacuzzi bathtub inside the bathtub. Our Studio is located one block from the famous International Dr. In Orlando City. In the center of everything!! Universal Studio’s area. FREE PARKING. -Universal Studio 8 minutes by car -Disney park’s 10 to 15 minutes by car. Airport 15 minutes by car. -Seaworld Park’s 8 minutes.

Guest favorite

A spacious living area features large glass doors that open to a scenic balcony overlooking the Arnold Palmer PGA golf course. Soft furnishings are complemented by a stylish coffee table and decorative accents. Nearby, a vibrant Star Wars-themed bedroom displays unique decor and multipurpose seating.

Condo in Kissimmee

4.95 out of 5 average rating, 167 reviews

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

This modern 3-bedroom luxury condo (with an ELEVATOR right to the door) has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Guest favorite

The master bedroom suite is spacious and features a king size bed adorned with blue and white accents. Two lamps are positioned on each side of the bed, with artwork displayed above. Natural light enters through the window, and a private bathroom can be seen through the open door.

Condo in Orlando

4.96 out of 5 average rating, 181 reviews

Luxury 2B2B APT Near Convention Center, Universal

*Location: On Universal BLVD, right next to International Dr Driving: 2 Min to Orange County Convention Center 7 Min to Sea World 12 Min to Universal Studio 15 Min to MCO airport 18 Min to Disney World Luxury 2b2b APT: (Designed by Danna) 1800 sqft, 2 King beds free community parking, gated community Access to community swimming pool, gym, sports court Free private wifi + spectrum cable TV We provide all supplies including towels, kitchen ware, cleaning supplies, shower supply

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 Orlando

4.97 out of 5 average rating, 144 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!!!

Top 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 Orlando

4.86 out of 5 average rating, 147 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.

Superhost

A modern living area features a sleek black sectional sofa positioned alongside a minimalist coffee table. Above, three framed artworks add visual interest, while potted plants provide a touch of greenery. Natural light filters through vertical blinds, enhancing the bright and airy ambiance.

Condo in Orlando

4.86 out of 5 average rating, 148 reviews

UPSCALE townhouse minutes to all attractions

LOCATION! LOCATION! LOCATION! You are going to be centrally located to all Orlando has to offer *Universal Studios less than 8 minutes *Seaworld is 7 minutes away *Disney world 18 minutes *Premium outlets about 8 minutes *MCO airport 20 minutes Conveniently located near major highways to commute anywhere in Orlando. The space is Fully renovated. There are 2 floors in this townhouse, the unit has a central AC that you can set your desired temperature to.

Superhost

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

4.82 out of 5 average rating, 102 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 spacious studio features a queen bed with a textured navy coverlet, complemented by bedside lamps. A cozy sleeper sofa is positioned near floor-to-ceiling windows that open to a balcony. A dining table with modern wooden chairs offers a comfortable seating area.

Condo in Florida Center

4.9 out of 5 average rating, 135 reviews

Studio near Universal & Epic, + Netflix, +parking

Renovated studio on I-Drive in 'The Enclave Hotel and Suites', free NETFLIX + parking Located 5 minutes from EPIC UNIVERSE and UNIVERSAL STUDIOS *no early check ins/late check outs, luggage hold/drop off or free mail/package delivery. Check out the page: usebounce *Please read entire listing/house rules. *The buildings have been renovated on the outside but on the inside they are very dated. If you are looking for a modern building this isn't it