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Apartment vacation 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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Guest favorite
A spacious studio is showcased with a king-size bed and a queen pull-out sofa. A smart TV is mounted on the wall. A dining table with blue chairs and a small coffee table add functionality to the layout. Soft lighting illuminates the modern decor.
Apartment in Orlando
4.82 out of 5 average rating, 161 reviews

NEW Designed Apt 2024 NrUCF PETSOk PrivateEntry

Discover this luxurious, newly renovated Airbnb studio with a FULLY PRIVATE patio featuring a hammock under a shady mango tree. Enjoy PRIVATE LAUNDRY, patio seating, and umbrella. The fenced backyard ensures privacy, minutes from UCF, Universal, Disney, and local amenities. The studio sleeps 4 and is part of a property with a house and a separate private apartment, each with its own kitchen, bathroom, bedroom, sitting room, garden hammock, patio, and entry. Experience tranquility in a quiet area

Top guest favorite
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.
Apartment in Orlando
5 out of 5 average rating, 205 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 favorite
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.
Apartment in College Park
4.93 out of 5 average rating, 305 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

Guest favorite
A charming exterior of a single-story home is shown, featuring a light blue façade and two large windows. A clear pathway leads to the front entrance, framed by lush green grass. A porch with two red chairs invites relaxation beneath the expansive oak trees overhead.
Apartment in Sanford
4.92 out of 5 average rating, 114 reviews

The Bed & Brad

Kick back and relax in this calm, stylish space. Enjoy the splendors of Sanford’s historic district with its beautiful brick roads and magnificent oak lined streets dripping with southern Spanish Moss. Walk or ride to the downtown area where you can eat and drink till your hearts content. Enjoy a walk along the lake or stroll through the streets to look at glorious restored southern homes. The Bed & Brad offers you all the comforts of home where you can enjoy your stay at your own pace.

Guest favorite
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.
Apartment in Winter Park
4.91 out of 5 average rating, 202 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.

Guest favorite
The entrance to Chris & Tish Suites features a welcoming red facade and a pair of double doors. Flanking the door, potted plants in vibrant colors are displayed, adding a touch of greenery. Decorative lanterns provide soft lighting, enhancing the inviting appeal.
Apartment in Eatonville
4.82 out of 5 average rating, 39 reviews

Cozy Town Suites B

Chris & Tish Suites: We have a partnership with traveling nurses and doctors. We are LESS than 2 minutes to get to the interstate-making it a breeze to get to and from the hospital. A super cozy and quiet apartment ALL to yourself! ( 1 bedroom with queen size bed and a shower). 26 minutes from DISNEY WORLD! This is the perfect central location. Less than 1 minute from Winter Park. Very quiet, newly renovated home in a Historic Town. Warm Regards, Chris & Tish

Guest favorite
A welcoming living room features a comfortable dark sofa accented by yellow pillows. A wooden coffee table sits in front, complementing the beige rug beneath. A glass desk with a chair is positioned near a window, with natural light illuminating the space. A 'WELCOME HOME' sign adorns the wall.
Apartment in College Park
4.9 out of 5 average rating, 126 reviews

Getaway in comfort with a pool

This excellent apartment has been furnished to a great standard. It’s the ideal retreat for a laid back & up-scale stay, located close to the absolute heart of Orlando. The neighborhood is known for its 20th-century cottages, abundant green spaces and lakes. Get ready to get inspired! Very close to some fabulous sites. All in all, guaranteed enjoyment and relaxation. All-day long. Settle in by zoning out with the four of you in a professionally cleaned home.

Top guest favorite
A modern living area features a vibrant red sofa and two gray armchairs, offering ample seating. A stylish coffee table sits centrally, complemented by a small plant centerpiece. A large television is positioned opposite the seating, with soft lighting from table lamps creating a welcoming ambiance.
Apartment in Clermont
4.98 out of 5 average rating, 128 reviews

Modern Suite in the Heart of Downtown Clermont 101

Experience luxury and excitement in our chic modern suite nestled in the vibrant heart of downtown Clermont. Perfectly poised for Triathletes, this suite is a beacon of comfort and convenience, mere steps away from charming downtown boutiques, delightful restaurants and local breweries. The location is unparalleled with close proximity to the celebrated Clermont/Minneola Trail, esteemed host of prestigious Triathlons and the serene Waterfront Park.

Guest favorite
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.
Apartment in Lake Dot
4.93 out of 5 average rating, 124 reviews

DT Orlando 1/1 Sunset View - 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)

Top guest favorite
An inviting living area features a comfortable light-colored couch, a dark wood dining table with four chairs, and rustic decor on the walls. Large windows allow natural light to fill the space, complemented by warm lighting fixtures. A kitchenette with open shelving is visible in the corner.
Apartment in Orlando
4.96 out of 5 average rating, 123 reviews

Wizard-Themed Condo Near Universal

Make some magical memories at this one-of-a-kind, intensely themed condo for witches and wizards of all ages, located just blocks away from Universal Studios and Universal Islands of Adventure. Between forays into the parks, relax at the pool and hot tub, grill up some savory delights, play basketball, or tone your abs in the gym. Then deepen your adventures with the large TV's, Playstation with Hogwarts Legacy, and other Harry Potter games.

Guest favorite
A light-filled living area features large windows adorned with soft sheer curtains. A dark sectional sofa is complemented by decorative pillows and a wooden coffee table in the center. A potted plant adds a touch of greenery, enhancing the inviting atmosphere.
Apartment in Holden/Parramore
4.88 out of 5 average rating, 204 reviews

2/2 PentHouse Downtown Orlando

This fully furnished 2/2 Penthouse, 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 bedrooms come with King beds. Our kitchen comes with pots, pans, plates and silverware, and has a FREE Nespresso for your morning wake up! We have our laundry machines in-house and yes, you can use them.

Top guest favorite
Apartment in Central Business District
4.67 out of 5 average rating, 9 reviews

Upscale King Suite in the Heart of Orlando w/ Pool

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in the heart of Orlando, FL! This stylish and cozy apartment is the perfect home base for your Florida getaway, offering a relaxing atmosphere and convenient access to nearby theme parks, shopping, and dining. Enjoy resort-style amenities and a comfortable stay in the center of Orlando. Please reach out for any potential multi-day discounts available

Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,339 GYDG$24,058 GYDG$18,828 GYDG$19,247 GYDG$17,782 GYDG$19,037 GYDG$19,665 GYDG$20,293 GYDG$18,619 GYDG$19,665 GYDG$21,966 GYDG$19,037 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about apartment rentals in Winter Park

  • Total vacation rentals

    Explore 60 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,270 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Winter Park vacation rentals include wi-fi 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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