Apartment vacation rentals in Winter Park

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!

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

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.

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 Ground-Floor 1BR | Sleeps 4 | Workspace

Ground-floor 1BR in Mills 50, Orlando’s walkable arts district 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. Spacious walk-in glass shower. Queen bed plus queen sofa sleeper; sleeps up to 4. Dedicated workspace, smart TVs in living room and bedroom. Free private and street parking.

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.

2Bedroom Haven Close to Parks KingBed PetFriendly

Welcome to our Modern 2-Bedroom, 2-Bathroom Apartment in Orlando! This chic and cozy apartment offers the ideal base for your Florida adventure. It combines comfort with convenience, featuring easy access to nearby theme parks, shopping, and dining options. Relax with resort-style amenities in the charming community. Sleeps 8 people! The whole apartment will be yours and NOT shared. Please reach out for potential multi-day discounts.

Apt A - Stylish Apt W POOL 3 BLOCKS FROM PARK AVE

Enjoy this PRIVATE and Sparkling clean entire home, first floor 2 bedroom/1 full bath luxury apartment near Park Avenue! Municipal golf course just a few blocks away. Many restaurants and bars nearby. Movie theatre just two blocks away, Publix supermarket two blocks away, Whole Foods 1/2 mile away and Trader Joe's 3/4 mile away. Fast internet speed: 139MBPS download and 21.5 MBPS upload!