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Apartment holiday rentals in Winter Park

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Quick stats about apartment rentals in Winter Park

  • Total holiday rentals

    Explore 10 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 470 verified reviews to help you choose

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Winter Park holiday rentals include wifi 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

Top-rated apartment rentals in Winter Park

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

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Guest favourite
Apartment in Orlando
4.95 out of 5 average rating, 138 reviews

Modern Lake view Condo 1 mile from Disney

You will love our updated 1 bedroom, 2 bathrooms, spacious 798 sq ft condo so close to Disney at Blue Heron Beach Resort in wonderful Lake Buena Vista, home to lots of restaurants and shopping! Enjoy spectacular sunrise views from your private balcony overlooking the lake. Resort amenities include large swimming pool, kiddie pool, hot tub, tiki bar, fitness rooms & game room. Located on peaceful Lake Bryan, you have access to water sports like kayaking, boating, jet skis & fishing on the lake.

Guest favourite
A dining area features a glass table surrounded by six upholstered chairs, creating a welcoming space. A sideboard is positioned against the wall, and artwork adorns the adjacent walls. Natural light filters in through a set of sliding glass doors, leading to the balcony.
Apartment in Orlando
4.9 out of 5 average rating, 308 reviews

Vista Cay Orlando Lakeview Condo

Modern luxury apartment (1800 sqft). 3 bedrooms, 2 bathrooms and 2 living rooms. Self catering. Sheets, pillows, towels, kitchen utensils are provided Corner balcony with view to Sea World Vista Cay has 2 pool areas with a nice club house, exercise room, game room, cinema, tennis/basket Easy checkin - guests receive a code to the condo so they are able to self-checkin without any delay on their arrival Local agent on site that can assist if there are any problems during your stay Free WI-FI

Top guest favourite
A bright living space showcases large windows with lake views, allowing natural light to fill the area. Two comfortable sofas and a round coffee table create a cozy seating arrangement. A dining table is visible nearby, along with modern decor and a wall-mounted TV.
Apartment in Orlando
4.96 out of 5 average rating, 109 reviews

Near Disney & Universal Parks, Stunning Lake Views

Just 1 mile to the "Welcome to Disney" property entrance & minutes to all Disney Parks, Universal, SeaWorld, and more! Two bedrooms, two full baths, bunk beds in a hallway alcove (each with a TV). Two balconies: East for stunning sunrises, west for sunsets and fireworks. Full kitchen, pool, hot tub, tiki bar. Free parking. NO RESORT FEE. Unit on 9th flr. Near Premium Outlet Mall, Convention Centers, Golf, Dining, Shops, Mini Golf, and Watersports. This is a perfect spot for an Orlando vacation

Guest favourite
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.
Apartment in Orlando
4.84 out of 5 average rating, 128 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 favourite
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.
Apartment in Orlando
4.93 out of 5 average rating, 240 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 favourite
A spacious terrace features comfortable lounge chairs with blue cushions and a stylish hanging chair. A small table accompanies two chairs, providing a perfect spot for relaxation. An umbrella offers shade, while the expansive view overlooks the surrounding area, enhancing the outdoor experience.
Apartment in Orlando
4.87 out of 5 average rating, 564 reviews

Lakefront Studio •Private Terrace• near Universal

Escape to this luxurious and serene studio retreat, featuring beautiful lake and pool views from your private terrace - the perfect spot to unwind after a day of adventure. Ideally located just off International Drive, you’ll be minutes from Orlando’s top attractions, dining, and shopping. Enjoy unbeatable convenience with Universal Studios and Epic Universe only 5 minutes away and Disney Parks just 15 minutes away. End the day by watching the Magic Kingdom fireworks from the terrace.

Guest favourite
Apartment in Orlando
4.86 out of 5 average rating, 204 reviews

Luxury Studio near to Epic Universe and Disney

Stylish, Newly Renovated Studio in the Heart of Orlando ✨ The perfect Orlando getaway in this beautiful studio with a king bed and full sofa bed. Fully renovated and designed to enjoy it. One block from International Drive and minutes from Universal Studios Florida, you’ll be right where all the action happens. 4 minutes to Universal Studios & Epic Universe 15 minutes to Walt Disney World Resort 5 minutes Premium & Prime Outlets for shopping 45 minutes to Cocoa Beach The best location❤️

Guest favourite
Apartment in Orlando
4.84 out of 5 average rating, 154 reviews

Cozy space 5/10 universal & epic

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!!

Guest favourite
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.
Apartment in Orlando
4.96 out of 5 average rating, 176 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 favourite
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.
Apartment in Winter Park
4.83 out of 5 average rating, 127 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 favourite
A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.
Apartment in Kissimmee
4.91 out of 5 average rating, 160 reviews

Modern Condo with Lake View Near Disney 3151

STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

Guest favourite
A bright and airy studio is showcased with large windows allowing natural light to fill the space. A king-size bed with a patterned quilt is paired with a comfortable daybed. A 65" TV is mounted on the wall, and a small dining area features two chairs with a vase of flowers.
Apartment in Orlando
4.8 out of 5 average rating, 113 reviews

XLPatio Studio/KingBed/Universal

2 miles from Universal Studios, 4 miles from SeaWorld, 9 miles from Disney, and 15 miles from Orlando International Airport . Located right on the famous International Drive . Steps away from Universal CityWalk . Oversized balcony with a partial fireworks view . King-size bed and a comfortable daybed . Mini kitchen . 65" 4K TV . High-speed WiFi . 24-hour self-check-in . Free parking . Access to resort pools and amenities

Popular amenities for Winter Park apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favourite
A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.
Apartment in Orlando
4.87 out of 5 average rating, 143 reviews

Luxury Condo On I-Drive & One Mile from Universal

Top guest favourite
A decorative display featuring a Mickey Mouse-shaped shelf with a deck of Bicycle playing cards. The shelf is flanked by two potted green plants, placed on a textured runner that complements the natural elements of the arrangement.
Apartment in Orlando
4.99 out of 5 average rating, 107 reviews

Classy Disney Themed Condo with FREE shuttle!

Superhost
Apartment in Kissimmee
4.85 out of 5 average rating, 105 reviews

Andris Luxury Homes Modern 1BR/1ba

Top guest favourite
An aerial view of the resort reveals a beautifully landscaped area with palm trees and pathways. The inviting outdoor pool is surrounded by lounge chairs, while nearby, a serene waterway meanders through the lush green landscape. The villas are nestled harmoniously among the greenery.
Apartment in Orlando
4.96 out of 5 average rating, 160 reviews

Marriott Sabal Palms 2BD Villa

Guest favourite
The living area features a comfortable sectional sofa arranged around a coffee table, with cushions for added comfort. Soft lighting is provided by table lamps, and a large window allows natural light to fill the space. Decorated with artwork and houseplants, the room offers a cozy atmosphere.
Apartment in Orlando
4.8 out of 5 average rating, 112 reviews

3BR Condo near Convention Center & Epic Universe

Top guest favourite
A modern studio presents a king-size bed with a plush gray comforter, elegantly complemented by a decorative throw. A cozy seating area features a blue tufted ottoman and stylish bar stools. Large windows allow natural light to fill the space, framed by sheer and dark curtains.
Apartment in Orlando
4.9 out of 5 average rating, 296 reviews

Maria Luz Studio-Huge Terrace/Universal area.

Top guest favourite
A spacious living area features a comfortable sectional sofa and a coffee table atop a textured rug. Light blue walls enhance the bright atmosphere, while artwork adorns the walls. The open kitchen includes wooden cabinetry and modern appliances, with seating available at the countertop.
Apartment in Orlando
4.96 out of 5 average rating, 112 reviews

Renovated Condo 2 miles away from Disney Lake view

Guest favourite
A stylish living room features a large gray sectional sofa complemented by bright orange cushions. A black coffee table stands in the center, while two lamps provide soft lighting. Wall decor includes mirrors and artwork, enhancing the airy ambiance created by the large windows.
Apartment in Orlando
4.8 out of 5 average rating, 168 reviews

Newly Renovated Premium Condo, Vista Cay - 2002

Pet-friendly apartment rentals

Guest favourite
Apartment in Davenport
4.88 out of 5 average rating, 114 reviews

Luxurious living just 15 min/Disney.

Superhost
Apartment in Orlando
4.78 out of 5 average rating, 27 reviews

Sunny FL Studio • Walk to Cafés • Near Downtown

Guest favourite
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.
Apartment in Orlando
4.94 out of 5 average rating, 129 reviews

Penthouse Lakeview Minutes to Disney/ Universal

Top guest favourite
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.
Apartment in Orlando
4.93 out of 5 average rating, 61 reviews

Stunning waterfront Views 1 mile to Disney 2 bath

Guest favourite
Apartment in Orlando
4.83 out of 5 average rating, 150 reviews

Designer 2BR Spacious Outdoor Space | Next to UCF

Guest favourite
Apartment in Horizon West
4.93 out of 5 average rating, 69 reviews

2BR Modern Pet-Friendly Condo 6 mins from Disney

Top guest favourite
The living area features a plush gray tufted sofa with decorative cushions, paired with a dark coffee table and a light area rug. A dining area with a sleek table and black chairs is visible in the background, alongside a modern kitchen with white cabinetry.
Apartment in Kissimmee
4.86 out of 5 average rating, 111 reviews

Wonderful apartment close to Disney • 3bed • 2bath

Guest favourite
Apartment in Orlando
4.83 out of 5 average rating, 6 reviews

Designer Luxury 1BR Condo - King Bed, Pool, Gym

Apartment rentals with a pool

Guest favourite
Apartment in Winter Park
4.95 out of 5 average rating, 39 reviews

Charming 2/1 Condo on a Lake in Winter Park

Top guest favourite
Apartment in Orlando
4.89 out of 5 average rating, 119 reviews

Lakefront Studio | Universal Views | Near I-Drive

Superhost
A spacious living area features a comfortable sofa and armchairs, accented by light streaming through large windows. A dining table with chairs is positioned beside a well-equipped kitchen, which can be seen in the background. Soft neutral tones create a serene atmosphere.
Apartment in Orlando
4.71 out of 5 average rating, 195 reviews

Inspiration @ South Pointe

Guest favourite
Apartment in Altamonte Springs
5 out of 5 average rating, 9 reviews

Condo in Altamonte springs

Guest favourite
A spacious outdoor pool is surrounded by lounges, with lush greenery and palm trees framing the scene. In the background, a multi-story condominium building is visible, set against a clear blue sky and soft clouds.
Apartment in Orlando
4.79 out of 5 average rating, 271 reviews

Beautiful Apartment 2 Bed 2 Bath Epic/ Universal

Guest favourite
Apartment in Orlando
4.91 out of 5 average rating, 183 reviews

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

Top guest favourite
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.
Apartment in Orlando
4.95 out of 5 average rating, 216 reviews

Luxury 2B2B APT Near Convention Center, Universal

Superhost
An aerial view of the scenic waterpark features winding lazy rivers, vibrant water slides, and lush palm trees. Sun loungers are arranged along the edges, offering a relaxing spot to unwind. A serene lake reflects the blue sky, enhancing the resort-like ambiance.
Apartment in Kissimmee
4.83 out of 5 average rating, 252 reviews

Disney 4 miles NEW * Heated LazyRiver & Pool*2B/2B

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