Apartment vacation rentals in Winter Park

Find and book unique apartments on Airbnb

Quick stats about apartment rentals in Winter Park

  • Total vacation rentals

    Explore 70 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,500 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

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 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

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 modern living area features a sleek leather sofa with decorative pillows, complemented by a glass coffee table. The wall displays a large fishing-themed artwork. Neutral tones accentuate the space, and a dining area with high chairs is visible in the background.
Apartment in Winter Park
4.96 out of 5 average rating, 235 reviews

Apt D -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. Simple elegance in downtown Winter Park defined by contemporary design and leisurely living. Heated pool, outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's best walking communities and do it in style! Fastest internet speed available: 177MBPS download and 21.5 MBPS upload

LocationFamilyCheck-in

Top guest favorite
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, 115 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.

FamilyValueAir conditioning

Top guest favorite
Apartment in Orlando
4.95 out of 5 average rating, 59 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.

FamilyLocationOutdoor spaces

Superhost
A modern living space features a large television mounted on a bright wall, adorned with vibrant floral artwork. A cozy gray sofa is accompanied by a coffee table on lush green carpet, while a dining table for four is set against a well-equipped kitchen backdrop.
Apartment in Winter Garden
4.88 out of 5 average rating, 102 reviews

StylishAptWtrGrdnOppLake&Prk&Yrd

*Brand new one bedroom apartment near downtown Winter Garden, across from Lake Apopka and Newton Park *Private fenced yard with BBQ, picnic table, and hammock. *Short golf cart ride to shops and restaurants in downtown Winter Garden *Opposite Newton Park with its breathtaking sunset views and many amenities (playground, public pool, boat ramp) and wildlife *Nearby Tanner Hall is available for private events and functions *Less than 30 min to Orlando Airport, Universal, Disney, and major malls

FamilyValueQuiet

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
5.0 out of 5 average rating, 246 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.

ValueLocationBackyard

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
4.92 out of 5 average rating, 371 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

FamilyValueDecor

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, 180 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!

ValueLocationAccuracy

Superhost
A spacious studio is furnished with a large bed and a blue couch. Elegant decor is highlighted by a chandelier above, while a backdrop of a city skyline adorns one wall. Natural light filters through large windows, creating an open and bright atmosphere.
Apartment in Orlando
4.87 out of 5 average rating, 391 reviews

Carmen Romantic Studio W/Private Beautiful Terrace

Beautiful Studio!! Amazing private TERRACE!! King side bed. Enjoy the Jacuzzi bathtub!! Our Studio It is located one block from the International Dr. in Orlando city in the center of everything!!Universal Studios area. 2 open swimming pools and 1 swimming pool with roof with tempered water. Enjoy the Gym and movies in Netflix!! This property is not recommended for children’s. I've been hosting and ‘’SUPERHOST’’ for 11 years. I'm completely focused on providing the best possible experience.

LocationValueAccuracy

Guest favorite
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.

LocationFamilyTV

Top 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
4.94 out of 5 average rating, 124 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.

LocationValueAccuracy

Guest favorite
Apartment in Orlando
5.0 out of 5 average rating, 5 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.

LocationFamilyParks

Top guest favorite
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, 117 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.

ValueFamilyAmenities

Popular amenities for Winter Park apartment rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,944 GYDG$18,408 GYDG$19,872 GYDG$19,872 GYDG$20,709 GYDG$22,591 GYDG$19,663 GYDG$20,290 GYDG$18,617 GYDG$19,663 GYDG$21,964 GYDG$19,035 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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