
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! 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.

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

The Johnson’s Apartments / Unit A
Relax with the whole family at this peaceful place to stay, since it is a Lake Front Apartment with an amazing view from inside. Aprox. 28 minutes from Walt Disney, Universal Studios, Sea World, Acuatica, Just 20 minutes from the Orlando Down Town, with a lot of great restaurants. Also, enjoy the Natural Springs of Wakiva, just 15 minutes way from this apartment,( a great place for visitors) Kitchen equipped with every thing. 1 bath / 1 queen size bed and a twin air bed for a third person.

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

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.

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.

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!

Lake Nona / Comfy Corner
We have a very comfortable place , centric location , close to any activity or necessity for our guests. One but not least, USTA Tennis Campus , DisneWorld, Universal Studios, Sea World, Aquatica, Children Hospital,Veteran Hospital, Restaurants, Parks, Theme Parks, Waterparks, MCO International Airport only 10 min Downtown Orlando, Florida Mall, last but not least Millennium Mall, Cocoa Beach, Tampa, Kennedy Space Center and way more! Just a drive away.,

Cozy Zen DT Orlando Apartment - 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)

Just 3 Blocks to Shops/Restaurants on Park Ave!
Modern, clean and unique. Fast internet speed: 263 MBPS download and 21.5 MBPS upload. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz countertops, high-end cabinetry and fixtures, great new furnishings and mattresses, 8' solid core interior doors, high ceilings, spacious open layout with a balcony offering fantastic sunset views and more! If you haven't explored Winter Park's Park Avenue, then you must!

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

Comfy Farm Studio Stay

*NEW* Villa Amalfi Boho• FreeParksShuttle•PoolView

Modern Orlando APT w/Laundry & Private Patio

3191-307 Resort Lake View Disney Universal Orlando

Yania's Cozy Getaway

Beautiful and Romantic Private Suite

Escape to Orlando near Universal Studios.
Private apartment rentals

"The Sweet Suite" - Private & Quiet, Near 408/417

Cozy Butterfly House

Lake Eola suite 2

Brand New Lakeside Retreat Apartment

Apartment in Altamonte Springs!

Charming Lakefront Apt. Near Disney

Cozy Apartment w/ Kitchen | Near Universal

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

2 Bedroom Illuminating Abode

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

BEST Views~2B2B~Universal~Disney

2 bedrooms 2 baths near Disney Universal Seaworld

Carmen Romantic Studio W/Private Beautiful Terrace

Modern 3 Bedroom Apartment Near the Theme Parks

Modern Luxury Kissimmee Retreat

BRAND NEW 2BR Apt, 5mi to Disney - Storey Lake 401
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £77 | £87 | £68 | £70 | £64 | £69 | £71 | £73 | £67 | £61 | £62 | £68 |
| 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 flat rentals in Winter Park

Total holiday rentals
Explore 60 holiday rentals in Winter Park

Nightly prices starting at
Winter Park holiday rentals start at £23 per night before taxes and fees

Verified guest reviews
Over 3,200 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
60 of Winter Park holiday rentals include wifi 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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- Apartment rentals Winter Park
- Fitness-friendly rentals Winter Park
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Disney's Animal Kingdom Theme Park
- Old Town Kissimmee
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Daytona International Speedway
- Universal's Volcano Bay
- Playalinda Beach
- Discovery Cove
- Aquatica
- Apollo Beach
- Island H2O Water Park
- Titusville Beach
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
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- Things to do United States
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