Apartment holiday rentals in Winter Park

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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

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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.

Cozy Convenience

Close to UCF, DISNEY, DOWNTOWN & KIA CENTER & CAMPING WORLD STADIUM! Keep it simple at this peaceful and centrally located place. Close to everything you need - 5 minutes to local Arcadia Acres Park, 20 minutes to the airport, 30 minutes to the theme parks. Very close to major expressways 417, I-4, and SR408! Convenience with a stocked kitchenette, free WiFi, Smart TV, Split A/C and heating. The spacious queen bed comfortably sleeps 2. *No smoking or pets allowed inside or outside the suite*

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!)

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Emerald Grove - Close to Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

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.

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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 🛋️

Cozy Chambers 2 Blocks From Park Ave With Pool

Cozy duplex connected to a gorgeous heated pool area with grill station in walkable downtown Winter Park! Just two blocks from bustling Park Avenue and all it's shops, restaurants, bars, cafes, Central Park, and Winter Park Station which serves both the SunRail and Amtrak trains.( Hornless train operation here in Central Florida, so no noise from that!) The Morse Museum, Scenic Boat Tours and Rollins College are all within easy walking distance! Bikes available.

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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.

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.

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Modern Luxury King Suite | Central Orlando + 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