
Condo vacation rentals in Winter Park
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Top-rated condo rentals in Winter Park
Guests agree: these condos are highly rated for location, cleanliness, and more.

Lake-front view at International Drive & Universal
Renovated Studio Apt with full size balcony, lake-front view & view of Universal Orlando. Located in heart of International Drive. World-class dining, attractions, shopping, entertainment & nightlife all within walking distance. Fully remodeled with many upgrades. Fully furnished with full-size refrigerator, kitchenette, queen bed, & sofa bed! Community has 3 pools & hot tubs, restaurant, basic gym, tennis, laundry facility ($), free wifi & free onsite parking. No "resort fee" or hidden charges.

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!

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.

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.

Location,Location 3bd 2bth near parks conv.ct/Int.
Beautiful updated 3bedroom 2 full bathrooms, sleeps 8; only 200 ft from club house. Located near Universal Studios, Sea World and within walking distance to Orange County convention center and International Drive. For your convenience we offer valet wagon for those heavy bags and electronic door lock for easy access. Our club house has a large hot tub, 2 pools ( 1 large adult and 1 large children's pool ), pools are heated during winter, poolside tiki bar, fitness room, gated community .

5 mins Universal 10 mins Epic park | Rustic LOFT
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!!

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!!!

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.

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.

Gorgeous Views: Golf Front, StarWars, XBox, 2Pools
This modern 3-bedroom luxury condo 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.

VC10-101 - 3 Bedrooms near Universal Studios
Welcome to VC10-101 at Vista Cay Resort! Get ready for an unforgettable Orlando getaway at our warm and inviting 3-bedroom, 2-bathroom condo, just minutes from all the magic. Whether you’re here to explore Disney’s Magic Kingdom, Universal Studios Orlando, or simply relax, this beautiful condo is the perfect home base for your adventures.

Lakefront Resort Studio -5 min to Universal
Modern, spacious studio with stunning lake views from a private balcony. Ideally situated for the ultimate Orlando vacation—just off International Drive and close to major attractions, theme parks, dining, and shopping. Only 5 minutes from Universal Studios/Epic Universe and 15 minutes from Disney. No deposit required and no extra fees.
Popular amenities for Winter Park condo rentals
Weekly condo rentals

Modern super clean condo at Ventura Country Club !

Delightful Central Studio w/Balcony & Kitchenette

Chic Oasis in heart of Orlando

London House | Orlando Airport Private Condo

Ventura Country Club Home away from home

2BD Champions Gate Magical Near Disney (CG 1177)

Renovated Condo Lake Eola View Great Location

Cozy, yet convenient for both business & holiday!
Pet-friendly condo rentals

Pet friendly Orlando area near ESPN Center

Penthouse Lakeview Minutes to Disney/ Universal

Westgate Palace Resort 2 bedroom

Home away from home for the Parks!

Private Studio near Conventions & Theme Parks

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Newly Renovated Premium Condo, Vista Cay - 2002

Storey lake, The Cove.
Condo rentals with a pool

Club Wyndham Bonnet Creek, 1 BR Deluxe

Studio near Epic & Universal, free parking

Lakefront Studio-Balcony- 6 mins to Universal-I-Dr

1 Bed 1 Bath Golf Resort Condo (2nd FL)

relaxing lake view escape

Magic Spring

Boho Retreat: 7 min to Universal & Epic!

Modern Lake view Condo 1 mile from Disney
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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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Give Kids the World Village
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Daytona International Speedway
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
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- Aquatica
- Island H2O Live!
- Disney's Hollywood Studios
- ICON Park
- Ocala National Forest
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