
Apartment holiday 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.

Private Rooftop Suite! No resort fees!
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.

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

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. Washing the video on YouTube: https://youtu.be/tJ1QXsomuY8 The resort has 2 open swimming pools and 1 swimming pool with a closed roof with tempered water. Pool hours may change due to COVID Enjoy the Gym and movies in Netflix! This property is not recommended for children’s

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.

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

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.

“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

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.

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)

1Bd Apt in Downtown w/ King Bed |office, Free Prkg
Experience the best of Orlando from this private 1BR getaway in the heart of downtown! 🌆 Walk to top restaurants, bars, and Lake Eola — yet enjoy peace and privacy tucked on a quiet street. ☕ Complimentary coffee, 🚗 free private parking (rare downtown!), ⚡ fast Wi-Fi, 💻 remote work desk, and a cozy KING SIZE bed make it ideal for business or leisure stays. Perfect blend of comfort, convenience, and location — everything you need just steps away!

Sunny Oasis *FreeParkShuttle*Boho-inspired retreat
Welcome to Sunny Oasis, your perfect escape in the heart of Orlando. Immerse yourself in a beautifully curated Boho ambiance, filled with natural textures, earthy tones, and sunlit spaces. Whether you’re relaxing after a day at the parks or enjoying a peaceful getaway, Sunny Oasis offers the comfort and serenity you deserve. Book your stay with us and experience the allure of Orlando’s attractions in a clean, serene, and superbly located getaway.

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.
Popular amenities for Winter Park apartment rentals
Weekly apartment rentals

Stay with Nory and Yuset

Cozy Town Suites B

Modern Orlando APT w/Laundry & Private Patio

Epic stay at Vista Cay!

Luxury King Suite Near Epic U: Pool & Gym Access

Cozy Calm Blue One | Downtown Stay

Thornton park paradise 1 bedroom Lake Eola

Modern Luxury Kissimmee Retreat
Private apartment rentals

Cozy Butterfly House

Penthouse With EPIC Views

Studio # 5 One bed, one sofa bed, no smoking 4 people

The Noir Getaway

3180-207 Resort Pool View Disney Universal Orlando

Stylish getaway on Lake Eola

Yania's Cozy Getaway

Premier Resort Condo Suite Near Universal & Disney
Apartment rentals with a hot tub

Modern Vacation Home Just Minutes from Disney 8

Relax in Cozy Apt 1/1 near to Disney

Magical Newly Renovated 10 minutes to Disney 2+2

Deluxe Studio I-Drive & Parks

2 bedrooms 2 baths near Disney Universal Seaworld

Westgate Lakes+Spa Studio Sleeps 4

Super Location

Modern 3 Bedroom Apartment Near the Theme Parks
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $172 NZD | $193 NZD | $151 NZD | $155 NZD | $143 NZD | $153 NZD | $158 NZD | $163 NZD | $150 NZD | $135 NZD | $138 NZD | $151 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about apartment rentals in Winter Park

Total holiday rentals
Explore 60 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at $50 NZD per night before taxes and fees

Verified guest reviews
Over 3,270 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
30 properties have a dedicated workspace

Wi-Fi availability
60 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
Destinations to explore
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- Rentals with lake access Winter Park
- Rentals with a hot tub Winter Park
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