Apartment holiday rentals in Winter Park

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

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!)

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

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.

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.

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.

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.

Charming King Suite, Near Universal & Pet-Friendly

Welcome to our Modern 1-Bedroom, 1-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. The whole apartment will be yours and NOT shared. Please reach out for potential multi-day discounts.

UCF home

Ask Us about Long Term Stays. Comfortable private place perfect for long stays (179 days). Lake access, 2 miles from UCF campus. Conveniently located 5 mins from Waterford Lakes Mall, 8 mins from Orlando Speed World Dragway, 15 mins to DT Orlando, 30 mins from Kennedy Space Center, 45 mins to Universal or Disney Parks. Gated parking, RVs friendly. We do not accept kids under 12.