Apartment vacation rentals in Winter Park

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

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

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

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.

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.

Lake Eola Thornton Park Studio with balcony

Rental agreement needs to be e-signed before check in & ID submitted for legality. Info will not be shared. Check in information will not be shared unless rental agreement is signed and valid ID submitted. Unit on second floor must climb stairs. 1 parking space included off street. Affordable, no-frills stay in an amazing location. Clean, simple, and budget-friendly — perfect if you value location over luxury. The cosmetics on the exterior of the home are a work in progress.

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)

Elvis Studio Near UCF | Private | EV | Parking

Step into your own Elvis-inspired stay, just minutes from UCF. Private entrance, cozy terrace, EV charger, and a thoughtfully designed space perfect for couples or solo travelers. 10 min to UCF, 15 min to Downtown & Stadium, 25–40 min to theme parks. Includes WiFi, workspace, full kitchen, washer/dryer, free parking, self check-in, and 24/7 host support. Complimentary champagne to welcome your stay 🍾

Upscale King Suite in the Heart of Orlando w/ Pool

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in the heart of Orlando, FL! This stylish and cozy apartment is the perfect home base for your Florida getaway, offering a relaxing atmosphere and convenient access to nearby theme parks, shopping, and dining. Enjoy resort-style amenities and a comfortable stay in the center of Orlando. Please reach out for any potential multi-day discounts available

Studio 407 | Near Parks, Downtown & Airport

Cozy studio ideal for couples or small families (2 adults + 1 child). Enjoy a comfortable sleeping area, equipped kitchenette, fast WiFi, and a modern, spotless bathroom. Ideal for relaxing after a day out. Prime location: 5 minutes to Downtown, 25 minutes to theme parks, 15 minutes to the airport. Clean, comfortable, and smooth check-in—everything you need for a stress-free stay!