Apartment holiday rentals in Winter Park

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.

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

Studio Apt. Free Breakfast. No clean fee. 2 Kings

2 King Sized Beds. 1 Bathroom. Sleeps 4. Private Studio Apartment attached to left side of hosts house with private equipped Kitchen, private Bathroom & Private Entrance off the left end of the house. Flat Screen smart TV. A one time supply of "make your own" breakfast foods including Eggs, Butter, Muffins/Bread, Jelly, Sausage (or Cheese), Fruit /Juice, Coffee, tea, cream & sugar are provided and included for free. Self Check in by digital key pad. Free parking on site. No cleaning Fee : )

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.

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.

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

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!)

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.

Elvis Studio Near UCF | Private | EV | Parking

Elvis-inspired private studio just minutes from UCF, ideal for couples, solo travelers, business trips, and university visits. Enjoy a private entrance, cozy terrace, full kitchen, workspace, fast Wi-Fi, washer/dryer, self check-in, and one designated parking space. Attached to the main house but fully separate. Shared Level 2 EV charger; availability may require coordination. 10 min to UCF, 15 min to Downtown Orlando, and 25–40 min to theme parks. Welcome champagne included. 🍾

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 🛋️

Mills 50 1BR | Sleeps 4 | Workspace | Free Parking

Modern 1BR in Mills 50, Orlando’s walkable arts district packed 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. Spa-style rainfall shower. Queen bed plus queen sofa sleeper; sleeps up to 4! Dedicated workspace, and two 65” smart TVs. Free private and street parking.

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)