Apartment vacation 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

Upstairs Apt - 1924 Craftsman in Historic Downtown

Welcome to your private retreat in beautiful downtown Orlando! Located in Lake Eola Heights, the city’s oldest neighborhood. This upstairs apartment has everything you need for a comfortable stay. Equipped with a full kitchen, large fridge, cooktop/oven, plush queen bed, and coffee. Private Entrance and dedicated parking on-site. Only blocks from Lake Eola Park, Thornton Park shops, Mills 50 District, Dr. Phillips Center, Sunrail Station, Kia Center and more. 15-30 min drive to theme parks!

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

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.

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 & 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.

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.

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 🍾