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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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Superhost
A serene pool area features clear water with a gentle wave design along the edge. Lush palm trees surround the space, providing a tropical feel. Sunlight reflects off the water, while a floating yellow duck adds a playful touch.
Apartment in Orlando
4.89 out of 5 average rating, 166 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, 2 TV’s , Netflix Amazon, sitting area, and and a small kitchen, We a Manual Slingshot available for rent, the rent for the Slignshot will be $170 per day. 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

Top guest favorite
Apartment in Orlando
5 out of 5 average rating, 111 reviews

Private Rooftop Suite! No resort fees! 5 star

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

Top guest favorite
The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.
Apartment in Kissimmee
4.97 out of 5 average rating, 153 reviews

3121-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

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
4.81 out of 5 average rating, 144 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
4.99 out of 5 average rating, 183 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
4.94 out of 5 average rating, 256 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 favorite
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.
Apartment in Altamonte Springs
4.96 out of 5 average rating, 333 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 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
4.9 out of 5 average rating, 176 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 favorite
A cozy sleeping area features a queen-size bed with a light textured coverlet. Green accent pillows add a splash of color. Shelves above display decorative items, while a bedside table holds a clock. Natural light filters through a window, enhancing the inviting ambiance.
Apartment in Orlando
4.91 out of 5 average rating, 348 reviews

“The Velvet Escape” Near Attractions & Airport

Get ready to enjoy your vacation in this chic and comfortable apartment in the heart of Orlando. Located directly in front of the Florida Mall, this home is a convenient 15-20 min drive from all the major attractions. This is a private apartment, with it's own free parking and fenced in patio. The open layout, with private full kitchen and private bathroom makes it perfect for couples, solo adventurers, and business travelers. The stay includes FREE wifi, Netflix, and full stocked kitchen

Top 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 Orlando
4.94 out of 5 average rating, 113 reviews

DT Orlando High-Rise Free Parking - 8 MIN FROM EDC

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)

Superhost
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 Orlando
4.88 out of 5 average rating, 192 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.

Superhost
The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.
Apartment in Clermont
4.8 out of 5 average rating, 289 reviews

Charming Lakefront Apt. Near Disney

Welcome to our Charming Lakefront Apartment, located in South Clermont, just 20 minutes from Downtown Orlando, Walt Disney World, and all the exciting Central Florida attractions. Nestled on the serene Lake Sawgrass, this peaceful countryside retreat offers fishing, kayaking, boating, and other watersports activities.

Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,281 GYDG$23,993 GYDG$18,777 GYDG$19,195 GYDG$17,734 GYDG$18,986 GYDG$19,612 GYDG$16,065 GYDG$16,900 GYDG$18,151 GYDG$17,108 GYDG$18,777 GYD
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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$6,259 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,200 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

Destinations to explore

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