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Apartment holiday rentals in Winter Park

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Winter Park

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

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Superhost
A spacious living area is highlighted with light wood flooring and a calming blue accent wall. A dining table with chairs accommodates four, complemented by a cozy sofa. Shelves display kitchen essentials, with a microwave and kettle positioned on a counter beneath decorative wall art.
Flat in Kissimmee
4.92 out of 5 average rating, 143 reviews

*KingSizeBed*NrDisney* 100%private*PetsOK

Relax in this 5-star studio, just 15 minutes from Disney, MCO Airport, Downtown, and Universal! Enjoy your private patio, dining under the stars or swaying in the hammock! Take in serene lake views and beautiful sunsets just steps away. With nearby shopping, dining, and local parks, this studio offers the perfect blend of tranquility and easy access to top attractions. Whether you’re here for a Disney vacation or a business trip, this is the ideal retreat for relaxation, comfort, and convenience

Top guest favourite
A cozy living area features a dark gray sofa and armchair, complemented by a light rug on the floor. A small desk with a chair sits against the wall, and a wall-mounted television is positioned above. Natural light pours in through the front door with a window.
Flat in Orlando
4.99 out of 5 average rating, 189 reviews

Parent's Retreat!

Whether working in the area, visiting your student or catching a UCF Sporting event. This pet friendly "Parent's Retreat" is just what you're looking for. Located less than 2 miles from campus. this apartment is a great place to land at the end of the day. Kitchen includes microwave, fridge, coffee maker and air fryer. This 380 sq ft newly remodeled mother-in-law suite has private entrance, patio and yard. Suite is completely closed off from the house and has keyless locks for easy check in.

Top guest favourite
A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.
Flat in College Park
4.94 out of 5 average rating, 267 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 pet fee No cleaning fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

Top guest favourite
A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.
Flat in Altamonte Springs
4.96 out of 5 average rating, 338 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

Top guest favourite
The bedroom features a spacious bed dressed in soft blue bedding, complemented by two bedside lamps on wooden tables. Decorative curtains with a water-themed design frame the window, while a subtle area rug adds texture to the room's original terrazzo flooring.
Flat in Winter Park
4.91 out of 5 average rating, 183 reviews

The Lake House

Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

Top guest favourite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Flat in Kissimmee
4.99 out of 5 average rating, 117 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Superhost
A modern living area is presented with a sleek brown sofa facing a stylish coffee table. A wall-mounted 50-inch smart TV is visible, alongside a fan overhead. Natural light streams through large windows, enhanced by light gray walls, creating a bright and welcoming space.
Flat in Orlando
4.79 out of 5 average rating, 369 reviews

✪ Fashionable ✔Location ✔Netflix ✔Parking ✔Wifi

You also will have ✔FREE parking ✔wifi ✔ Netflix. All at an unbeatable price. Classy, clean and crisp modern decor. Bright white and gray fabrics, with warm golden metal accents. Snug and personal with stylish interior decor, you won't want to leave! Excellent location, 15 minutes from downtown Orlando, Amway Center, Winter Park, UCF and the airport. The theme parks are just less than 30 mins away too. Ideal for small groups, business travel, and traveling with children.

Top guest favourite
A well-appointed bedroom is highlighted by a spacious bed with a light-colored quilt. Flanking the bed are two lamps on wooden nightstands. Natural light filters through a large window, adorned with sheer curtains. A decorative mirror and wall art complement the serene atmosphere.
Flat in Orlando
4.95 out of 5 average rating, 123 reviews

Bright & Spotless. Private Apartment

Your Private Orlando Retreat. * (No shared spaces.) * Enjoy complete privacy in your own bedroom, bathroom, living room, kitchen, private entrance, and patio—no shared spaces. * Situated in a quiet, welcoming neighborhood just minutes from Waterford Lakes Town Center’s dining and shopping. * Close to UCF and major highways, offering an easy drive to Orlando’s top attractions, including Disney, Universal, and SeaWorld. Perfect for comfort, convenience, and relaxation.

Top guest favourite
A white door is adorned with a decorative wreath featuring white flowers and greenery. Adjacent to the door, a wooden sign with a rustic finish displays the word 'HOME' in large, bold letters, creating a welcoming entryway.
Flat in Orange County
4.9 out of 5 average rating, 282 reviews

Lake Nona / Comfy Corner

We have a very comfortable place , centric location , close to any activity or necessity for our guests. One but not least, USTA Tennis Campus , DisneWorld, Universal Studios, Sea World, Aquatica, Children Hospital,Veteran Hospital, Restaurants, Parks, Theme Parks, Waterparks, MCO International Airport only 10 min Downtown Orlando, Florida Mall, last but not least Millennium Mall, Cocoa Beach, Tampa, Kennedy Space Center and way more! Just a drive away.,

Guest favourite
A spacious living area is complemented by a modern kitchen featuring white cabinetry and stainless-steel appliances. A dark sectional sofa with decorative pillows faces the kitchen island, which is paired with two sleek bar stools. Large windows allows ample natural light.
Flat in Orlando
4.92 out of 5 average rating, 119 reviews

Cozy Zen DT Orlando Apartment - Free Parking

Welcome to Downtown Orlando, the City Beautiful! Enjoy the space of this peaceful, high rise apartment with a beautiful sunset view. Perfect for a weekend stay with nightclubs, bars, concert venues, arenas/stadiums and many restaurants nearby. - KIA Center (7 min) - Dr. Phillips Center (6 min) - Camping World Stadium/EDC Tinker Field (7 min) - Central Florida Fairgrounds (10 min) - Orlando City Soccer Stadium (5 min) - Universal Studios (16 min)

Guest favourite
A comfortable living area features a sectional sofa adorned with cushions in shades of yellow, teal, and deep purple. Two small tables sit in front, accompanied by a patterned area rug, while decorative wall art adds visual interest. Natural light filters through a window with blinds.
Flat in Bay Lake
4.94 out of 5 average rating, 110 reviews

Charming Oasis 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Superhost
Flat in Orlando
4.88 out of 5 average rating, 171 reviews

Apartment, 7 Min to Orlando Airport/ Lake Nona

Complete private unit . A Private Door inside the room to step out to the pool .1 Bed/1 Bath, Pool area will be available all the time .We just build a door inside the room that way is easy access. This place is 25 Minutes driving to Disney World and most Parks, Lake Nona is 10 minutes away. We are Close to UCF, lake Nona, MCO, Waterford lakes

Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

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Avg. price€ 88€ 99€ 77€ 79€ 73€ 78€ 81€ 83€ 76€ 69€ 70€ 77
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Quick stats about flat rentals in Winter Park

  • Total holiday rentals

    Explore 60 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 3,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Winter Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests – averaging 4.8 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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