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Apartment vacation rentals in Winter Park

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Top-rated apartment rentals in Winter Park

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

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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, 221 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, 326 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 canopy-covered terrace is accented by a comfortable seating area featuring plush blue cushions. Sun loungers are arranged alongside a dining table with umbrella, offering views of the surrounding landscape and sky.
Apartment in Orlando
4.92 out of 5 average rating, 104 reviews

Penthouse With Epic Views

Escape to a stunning, designer-remodeled 2BR/2BA penthouse with breathtaking views of the lake and four theme parks. This luxurious retreat comfortably fits 4 and features a private, wrap-around rooftop terrace, a kitchen, and full access to resort amenities like pools, a gym, and tennis courts. Perfect for a luxury vacation, this premier unit at The Enclave offers an unforgettable experience with high-end finishes and a dedicated workspace, combining comfort with unparalleled style.

Top guest favorite
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.
Apartment in Kissimmee
4.99 out of 5 average rating, 147 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!

Top guest favorite
A comfortable living area features a spacious couch with reclining sections and soft cushions. A Smart TV is placed on a black media console next to a stylish clock, while light filters through striped curtains. A small table holds a notepad, providing additional convenience.
Apartment in Minneola
4.97 out of 5 average rating, 146 reviews

Spacious Apartment In Minneola

This spacious 1 bedroom / 1 bathroom apartment is located West of Orlando in the beautiful town of Minneola right next to Clermont in the heart of Central Florida and is perfect for a short or long term stay. Features a large bedroom & bathroom, comfortable couch w/ dual recliners, plenty of closet space & storage, and a Smart TV. Kitchen is stocked with all the essentials and has a dishwasher, gas stove, refrigerator w/ ice maker, coffee maker, microwave and crockpot.

Top guest favorite
An aerial view of a rectangular swimming pool is surrounded by a stone patio. Lounge chairs are placed on either side of the pool, which is flanked by vibrant red bougainvillea flowers. A covered area with a sloped roof is visible in the foreground.
Apartment in Winter Park
4.91 out of 5 average rating, 148 reviews

Apt F -Modern Elegance in the Heart of Winter Park

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Pool, outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. The pool and grill stations are shared. Fast internet speed: 139MBPS download and 21.5 MBPS upload!

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
4.99 out of 5 average rating, 135 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 Orlando
4.93 out of 5 average rating, 127 reviews

DTO Sunset View Free Parking-15 Min From Universal

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 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 Orlando
4.88 out of 5 average rating, 206 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 Orlando
4.94 out of 5 average rating, 102 reviews

2Bedroom Haven Close to Parks KingBed PetFriendly

Welcome to our Modern 2-Bedroom, 2-Bathroom Apartment in Orlando! This chic and cozy apartment offers the ideal base for your Florida adventure. It combines comfort with convenience, featuring easy access to nearby theme parks, shopping, and dining options. Relax with resort-style amenities in the charming community. Sleeps 8 people! The whole apartment will be yours and NOT shared. Please reach out for potential multi-day discounts.

Guest favorite
Apartment in Orlando
4.89 out of 5 average rating, 193 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

Top guest favorite
The living area features a light-colored sofa and two patterned armchairs arranged around a small coffee table. Natural light fills the space through multiple windows, with a television placed on a dark wood console. Framed artwork adorns the walls, adding visual interest.
Apartment in Windermere
4.99 out of 5 average rating, 113 reviews

Relaxing 2BR Lakeview Retreat Close to Attractions

Relaxing getaway with gorgeous lake views in historic Windermere just minutes from Disney, Universal, and all Orlando-area attractions. Skip the tourist traps and retreat to this charming, newly renovated apartment in quiet, old Florida. Perfect for families visiting the parks or anyone seeking a quiet getaway.

Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ375ﺩ.ﺇ422ﺩ.ﺇ331ﺩ.ﺇ338ﺩ.ﺇ312ﺩ.ﺇ334ﺩ.ﺇ345ﺩ.ﺇ356ﺩ.ﺇ327ﺩ.ﺇ345ﺩ.ﺇ386ﺩ.ﺇ334
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 ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 3,370 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 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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