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Apartment holiday rentals in Winter Park

Find and book unique apartments on Airbnb

Quick stats about apartment rentals in Winter Park

  • Total holiday rentals

    Explore 70 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,500 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Winter Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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

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
A welcoming entrance of the Vista Cay resort features a central fountain surrounded by lush palm trees and well-maintained landscaping. The brick pathway leads towards the clubhouse, highlighting the resort's inviting atmosphere and access to amenities.
Apartment in Orlando
4.94 out of 5 average rating, 116 reviews

Your condo next to Universal epic universe

This 1247 sq/ft condominium is part of Vista Cay Orlando Fl. I keep my condo clean and in excellent condition for all of my guests. The condominium is centrally located within the entertainment and attractions district of Orlando, only minutes from International drive ,Sea World the Orange county convention center and just 9 minutes from Universal and 15 minutes from Disney. You'll have quick access to great restaurants shops and many local attractions.We just opened up a new pool its beautiful.

LocationFamilyCheckout

Top Guest favourite
Apartment in Orlando
4.95 out of 5 average rating, 60 reviews

Epic stay at Vista Cay!

This 2-bedroom, 2-bathroom apartment at Vista Cay Resort, Orlando, offers an exceptional location for enjoying the best of the city. Just minutes from Orlando International Airport and Walt Disney World, it provides unparalleled convenience for both travelers and residents. Additionally, its proximity to the Convention Center, Universal Studios, SeaWorld, and International Drive grants easy access to major attractions, dining, and shopping, offering a complete experience in the heart of Orlando.

LocationFamilyParks

Top Guest favourite
Apartment in Winter Park
4.92 out of 5 average rating, 88 reviews

Orlando Small Budget Minded Clean Private Eff. Apt

Enjoy this quiet clean efficiency APARTMENT (within 1 mile of Downtown Orlando - Orlando is across the street). Apartment is 1 mile of 113 eating establishments, in a great neighborhood, clean (never any pets) very centrally-located. Not extravagant or beautiful, just a clean no hassle relaxing stay. All you need at a bargain price. Near: shopping, Bus, Train, churches, golf course, Famous Park Ave Winter Park, Hospitals, parks, attractions, museums, major hwy interchanges + Easy on easy off I-4

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Guest favourite
A comfortable living area features a light-colored sofa adorned with decorative pillows. A round coffee table sits in front, complemented by a plant centerpiece. Two abstract artworks in gold and blue are displayed on the walls, while a full-length mirror leans against one side.
Apartment in Orlando
4.98 out of 5 average rating, 106 reviews

Modern Orlando APT w/Laundry & Private Patio

Newly Built Apartment. Attached to the main house completely private bedroom, living room with 50" Roku TV, kitchen, washer & dryer. Water Softener System in Property. Private entrance and private patio with no sharing areas. Within minutes of Rio Pinar Golf, Waterford Lakes Town Center, UCF, Valencia College East Campus & Orlando MCO Airport. Plenty of nearby restaurants as well as close distance to major highways for easy access to all theme parks. Enjoy the tranquility of our neighborhood.

ValueLocationQuiet

Guest favourite
A welcoming bedroom features a queen bed covered with an orange bedspread and decorative pillows. A colorful rug lies underneath, complementing the warm tones. A doorway leads to the kitchenette, which is partially visible, showcasing shelves and appliances. A ceiling fan provides comfort in the well-lit space.
Apartment in College Park
4.92 out of 5 average rating, 377 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard & entrance w/ easy checkin. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s an AC unit in the Airbnb, large TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $30 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 Rollins College 1.9

ValueFamilySleep quality

Superhost
A private terrace is presented with ample lounge chairs facing a scenic waterfront view. Lush greenery surrounds the area, and a bright blue sky is visible above, enhancing the open atmosphere. The cityscape with buildings is visible in the distance.
Apartment in Orlando
4.84 out of 5 average rating, 181 reviews

BEST Views~2B2B~Universal~Disney

!! GREAT LOCATION !! Elegant, gorgeous 2B2B condo close to everything! PRIVATE 270-degree HUGE terrace with the best views in Orlando! Clear view of Disney fireworks! Both bedrooms have resort-level amenities. The master bedroom features dedicated makeup space and Tempur-Contour memory foam mattress. The living room has a cozy daybed for extra guest or as a coach. All the rooms can see Volcano Bay! Our kitchen provides basic as well as cool amenities: cup washer. Book for family and friends!

ValueFamilyNearby

Guest favourite
Apartment in Orlando
5.0 out of 5 average rating, 11 reviews

Luxury 2BR Suite l Downtown, Pool, Gym, Games!

Welcome to this first floor apartment with direct sidewalk entry for your modern getaway in the heart of Orlando! Whether you're here for business, family, or fun, this space has everything you need for a memorable stay. This 2 Bedroom, 2 Bathroom Suite Features: - Rooftop Pool with cabanas and sun loungers - Private arcade machine - Sky lounge - Courtyard with hammocks & outdoor games - Community Game-Room - Fitness Center - Dedicated work center - Fire pits (Add us to your Wishlist!)

LocationFamilyAmenities

Guest favourite
Apartment in Winter Park
4.9 out of 5 average rating, 229 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.

LocationValueGetting around

Top Guest favourite
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
4.94 out of 5 average rating, 126 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.

LocationValueLong stay

Superhost
A modern studio space features a king-size bed with a blue blanket and decorative pillows. The kitchen area includes white cabinets and stainless steel appliances. A dining table with four chairs is positioned nearby, and a large TV is mounted on the wall. Natural light fills the room.
Apartment in Orlando
4.84 out of 5 average rating, 109 reviews

NEW5*APT⛱NrUCF*PETSOK+PRIVATE patioENTRY+LAUNDRY⛱

✨ 5⭐ Luxury Studio Near UCF & Universal ✨ Relax in a fully renovated studio perfect for executives, Disney visitors, or UCF trips. 🏡 Key Features: • 🌳 Private fenced yard with hammock & dining area 🍽️ • 🚪 Private entry & patio for complete privacy • 🧺 In-unit washer & dryer for convenience • 📶 Fast Wi-Fi, 🚗 free off-street parking, & modern furnishings • 🎢 25 mins to Universal, 🛍️ close to shopping & dining 🛌 Sleeps 4: • King-size bed 🛏️ • Queen pull-out sofa 🛋️

ValueLocationBackyard

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

Mills 50 Ground-Floor 1BR | Sleeps 4 | Workspace

Ground-floor 1BR in Mills 50, Orlando’s walkable arts district with murals, eclectic restaurants and nightlife; on the border of Audubon Park Garden District (Leu Gardens, East End Market). Minutes to Downtown Orlando, AdventHealth, and Baldwin Park. 12 minutes to Kia Center and Camping World Stadium. Spacious walk-in glass shower. Queen bed plus queen sofa sleeper; sleeps up to 4. Dedicated workspace, smart TVs in living room and bedroom. Free private and street parking.

FamilyLocationLong stay

Top Guest favourite
The living area features a spacious sectional sofa with rich teal upholstery and colorful accent pillows. Vibrant artworks adorn the walls, while decorative string lights create a warm atmosphere. A unique white sculptural chair and a low coffee table complete the eclectic and inviting space.
Apartment in Thornton Park
4.98 out of 5 average rating, 119 reviews

Walk to Lake Eola 2 BR Balcony Apt + Free Parking

Stay in the heart of Thornton Park — walk to Lake Eola, downtown dining, nightlife, and coffee shops from this bright 2BR balcony apartment with free parking. Step into elegance & comfort in our spacious 2 bedroom apartment w/ two majestic king beds awaiting your indulgence. From the opulent furnishings, to the unique decor every detail is hand curated & whispers sophistication. We promise an extraordinary stay where luxury meets hospitality in every moment.

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Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

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Avg. price$112 AUD$122 AUD$132 AUD$132 AUD$137 AUD$150 AUD$130 AUD$134 AUD$123 AUD$130 AUD$145 AUD$126 AUD
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Destinations to explore