Apartment holiday rentals in Winter Park

A welcoming entrance of the Vista Cay resort features a central fountain surrounded by lush palm trees and well-maintained landscaping. The brick pathway leads towards the clubhouse, highlighting the resort's inviting atmosphere and access to amenities.

4.94 out of 5 average rating, 117 reviews

Your condo next to Universal epic universe

This 1247 sq/ft condominium is part of Vista Cay Orlando Fl. I keep my condo clean and in excellent condition for all of my guests. The condominium is centrally located within the entertainment and attractions district of Orlando, only minutes from International drive ,Sea World the Orange county convention center and just 9 minutes from Universal and 15 minutes from Disney. You'll have quick access to great restaurants shops and many local attractions.We just opened up a new pool its beautiful.

4.95 out of 5 average rating, 60 reviews

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.

5.0 out of 5 average rating, 14 reviews

Flat in Winter Garden

Modern Luxury Stay | 20 min 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 minutes away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

Superhost

A private terrace is presented with ample lounge chairs facing a scenic waterfront view. Lush greenery surrounds the area, and a bright blue sky is visible above, enhancing the open atmosphere. The cityscape with buildings is visible in the distance.

4.84 out of 5 average rating, 181 reviews

BEST Views~2B2B~Universal~Disney

!! GREAT LOCATION !! Elegant, gorgeous 2B2B condo close to everything! PRIVATE 270-degree HUGE terrace with the best views in Orlando! Clear view of Disney fireworks! Both bedrooms have resort-level amenities. The master bedroom features dedicated makeup space and Tempur-Contour memory foam mattress. The living room has a cozy daybed for extra guest or as a coach. All the rooms can see Volcano Bay! Our kitchen provides basic as well as cool amenities: cup washer. Book for family and friends!

5.0 out of 5 average rating, 11 reviews

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!)

4.94 out of 5 average rating, 98 reviews

Flat in Thornton Park

Historic Home Lake Eola Studio Thornton Park

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 1 off street parking space included Owner lives in another unit on premise The cosmetics on the exterior of the house are a work in progress Affordable, no-frills stay in an amazing location. Clean, simple, and budget-friendly—perfect if you value location over luxury

4.9 out of 5 average rating, 229 reviews

Flat in Winter Park

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.

A canopy-covered terrace is accented by a comfortable seating area featuring plush blue cushions. Sun loungers are arranged alongside a dining table with umbrella, offering views of the surrounding landscape and sky.

4.94 out of 5 average rating, 127 reviews

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.

4.93 out of 5 average rating, 29 reviews

A tranquil outdoor space showcases a heated pool surrounded by a stone patio. Lounge chairs are positioned nearby, and vibrant bougainvillea adds color to the scene. The pale walls of the structure reflect daylight, while large windows offer views into the interior.

Flat in Winter Park

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.

4.98 out of 5 average rating, 122 reviews

The living area features a spacious sectional sofa with rich teal upholstery and colorful accent pillows. Vibrant artworks adorn the walls, while decorative string lights create a warm atmosphere. A unique white sculptural chair and a low coffee table complete the eclectic and inviting space.

Flat in Thornton Park

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.

Superhost

5.0 out of 5 average rating, 7 reviews

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.