Apartment holiday rentals in Winter Garden

Stay A While

Welcome to Your Secluded Getaway, which has been recently updated in July 2026. Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont 14m Outlets: 28m | Florida Mall: 35m | I-Drive: 40m Travel MCO Airport: 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks storage only

Family · Value · Indoor spaces

Luxury 2BR | Pool, Gym, Near 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.

Location · Hospitality · Comfort

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

Family · Value · Pets

Studio Apt. Free Breakfast. No clean fee. 2 Kings

2 King Sized Beds. 1 Bathroom. Sleeps 4. Private Studio Apartment attached to left side of hosts house with private equipped Kitchen, private Bathroom & Private Entrance off the left end of the house. Flat Screen smart TV. A one time supply of "make your own" breakfast foods including Eggs, Butter, Buiscuits/Bread, Jelly, Sausage or Cheese, Fruit /Juice, Coffee, tea, cream & sugar are provided and included for free. Self Check in by digital key pad. Free parking on site. No cleaning Fee : )

Family · Value · Walkability

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!

Value · Family · Hospitality

Cozy studio at The Enclave Hotel & Suites Orlando

Cozy studio Recently renovated with granite finishes, in this studio you will find a complete kitchen, one bathroom, dining area, sofa bed and a queen size bed. Centrally located by International Drive, this studio is inside of The Enclave resort. The resort has 2 open swimming pool and 1 swimming pool with a closed roof with tempered water. whether you are coming to Orlando to visit Theme parks or looking for "me time" and relaxation, this studio is suited for creating lovely memories.

Location · Value · Indoor spaces

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.

Family · Value · TV

Apartment in Four Corners

Escape to this stylish 2-bedroom, 2-bathroom condo, perfect for families or friends seeking a memorable getaway. Enjoy spacious living area, complete with a comfortable sofa bed, and a fully-equipped kitchen. Relax in luxury with a king-size bed and en-suite bathroom. Access at NO ADDITIONAL cost to world-class pools, a lazy river, and a fitness center . Enjoy complimentary Wi-Fi and parking Located in the heart of Champions Gate, Aprox. 15 mins to Disney Parks & 30mins to Universal

Location · Value · Pets

Premier Clermont Suite /Prime Downtown 103

Immerse yourself in the sophisticated serenity of our strategically located prime suite, nestled in the vivacious heart of downtown Clermont. elegantly appointed with meticulous attention to detail our suite offers a harmonious blend of opulence and home-like comfort-whichever way you look, every corner is designed to offer an unrivalled stay experience. This property is a dream come true for Triathletes! Standing right at the epicenter of Clermont.

Value · Family · Checkout

Close to Parks Retreat with KingBed & 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.

Family · Location · Checkout

Great Full Apartment. Just 5' from Disney Orlando

Fantastic apartment in a nice and quiet place. Private gate area with security, locate in the best resort of Kissimmee: Legacy Dunes. Only 4 milles from Disney Parks. Full kitchen, laundry, central A/C, 2 bedroom, 2 bathrooms. Living room, dining room, balcony. Climatized pool, club house, fitness area, tennis court, childs área, free parking and wifi.

Value · Family · Air conditioning

Cozy Modern 1 Bedroom Apartment

Warm welcome to our modern one bedroom apartment. We are happy to be your host for your stay. Located minutes away from attractions such as Walt Disney World and Universal Studios. During your stay you will find comfort with a brew of a delicious cup of coffee as the sun rises. Book your next stay with us. We would love to be your host!

Value · Family · Checkout