Apartment holiday rentals in Winter Park

A cozy living area features a dark gray sofa and armchair, complemented by a light rug on the floor. A small desk with a chair sits against the wall, and a wall-mounted television is positioned above. Natural light pours in through the front door with a window.

5 out of 5 average rating, 220 reviews

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.

4.93 out of 5 average rating, 325 reviews

A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.

Flat in College Park

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 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 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

4.97 out of 5 average rating, 146 reviews

A comfortable living area features a spacious couch with reclining sections and soft cushions. A Smart TV is placed on a black media console next to a stylish clock, while light filters through striped curtains. A small table holds a notepad, providing additional convenience.

Flat in Minneola

Spacious Apartment In Minneola

This spacious 1 bedroom / 1 bathroom apartment is located West of Orlando in the beautiful town of Minneola right next to Clermont in the heart of Central Florida and is perfect for a short or long term stay. Features a large bedroom & bathroom, comfortable couch w/ dual recliners, plenty of closet space & storage, and a Smart TV. Kitchen is stocked with all the essentials and has a dishwasher, gas stove, refrigerator w/ ice maker, coffee maker, microwave and crockpot.

4.98 out of 5 average rating, 104 reviews

A modern living area features a cozy gray sofa draped with a textured throw, complemented by a wooden coffee table. An open kitchen with bar seating is visible, along with neutral walls and tile flooring, providing a spacious and bright environment.

Flat in Clermont

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.

A spacious living area is complemented by a modern kitchen featuring white cabinetry and stainless-steel appliances. A dark sectional sofa with decorative pillows faces the kitchen island, which is paired with two sleek bar stools. Large windows allows ample natural light.

4.93 out of 5 average rating, 127 reviews

DTO Sunset View Free Parking-15 Min From Universal

Welcome to Downtown Orlando, the City Beautiful! Enjoy the space of this peaceful, high rise apartment with a beautiful sunset view. Perfect for a weekend stay with nightclubs, bars, concert venues, arenas/stadiums and many restaurants nearby. - KIA Center (7 min) - Dr. Phillips Center (6 min) - Camping World Stadium/EDC Tinker Field (7 min) - Central Florida Fairgrounds (10 min) - Orlando City Soccer Stadium (5 min) - Universal Studios (16 min)

Flat in Lake Eola Heights

An inviting living area features two spacious blue sofas surrounding a light, triangular coffee table. A large area rug with warm tones adds comfort, while a flat-screen TV is mounted on the wall. A wooden dining table is visible in the corner, with natural light filtering in through the windows.

4.8 out of 5 average rating, 112 reviews

1Bd Apt in Downtown w/ King Bed |office, Free Prkg

Experience the best of Orlando from this private 1BR getaway in the heart of downtown! 🌆 Walk to top restaurants, bars, and Lake Eola — yet enjoy peace and privacy tucked on a quiet street. ☕ Complimentary coffee, 🚗 free private parking (rare downtown!), ⚡ fast Wi-Fi, 💻 remote work desk, and a cozy KING SIZE bed make it ideal for business or leisure stays. Perfect blend of comfort, convenience, and location — everything you need just steps away!

A light-filled living area features large windows adorned with soft sheer curtains. A dark sectional sofa is complemented by decorative pillows and a wooden coffee table in the center. A potted plant adds a touch of greenery, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 206 reviews

2/2 PentHouse Downtown Orlando

This fully furnished 2/2 Penthouse, comes fully equipped with all the necessities you need for your vacation or short stay to Orlando, The City Beautiful. We have fully remodeled our house and would like to share the experience with you. The bedrooms come with King beds. Our kitchen comes with pots, pans, plates and silverware, and has a FREE Nespresso for your morning wake up! We have our laundry machines in-house and yes, you can use them.

4.94 out of 5 average rating, 101 reviews

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.

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.

4.92 out of 5 average rating, 104 reviews

Penthouse With EPIC Views

A 2024 full remodel by Luiz Durand of the most expensive unit ever sold at The Enclave. Sun rises, a wrap around private terrace and views over 4 theme parks combine to make this a vacation experience unlike any other. Granite and travertine throughout. Stainless steel appliances and oversized smart TVs. Hotel amenities include indoor and outdoor pools, tennis, food court, pub and gym.

4.93 out of 5 average rating, 104 reviews

A spacious living area is illuminated by natural light filtering through large windows. Comfortable seating includes a grey couch and a pair of blue armchairs. A flat-screen television is positioned on a metallic stand, while a glass coffee table sits atop a patterned area rug.

Flat in Thornton Park

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. The cosmetics on the exterior of the home are a work in progress.

4.88 out of 5 average rating, 32 reviews

Flat in Winter Park

Apartment| Downtown Orlando 10 min & Disney 25 min

1ST FLOOR APARTMENT: The Garden Suite 🌻 Discover your peaceful Winter Park hideaway! Enjoy easy access to Orlando's best: Disney (25 min), Universal (19 min), Kia Center (10 min), Downtown Orlando (10 min) and Downtown Winter Park (6 min) Perfect for couples, families or solo travelers looking to relax and explore. Your home away from home!

4.8 out of 5 average rating, 472 reviews

A spacious studio room features a king bed with decorative bedding and a leather sofa. Natural light filters through the sheer balcony curtains, and a wooden desk with a chair is positioned near the window. The warm-toned walls complement the patterned carpet.

Flat

Westgate Lakes+Spa Studio Sleeps 4

Offering a 493 sq foot studio with a King Bed Queen Sleeper Sofa, & Kitchenette in Westgate Lakes Resort & Spa. Ideally located close to the Orlando area attractions and with amazing on site amenities Westgate Lakes & Spa is a fabulous place to stay.

Popular amenities for Winter Park apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.99 out of 5 average rating, 93 reviews

Stay with Nory and Yuset

4.84 out of 5 average rating, 57 reviews

A comfortable living area is highlighted by a light grey sofa and a wooden media console. A large flat-screen TV is mounted on a vibrant green wall. Natural light filters through large windows adorned with blinds, illuminating a small plant and decorative elements on the console.

Flat in South Eola

Stylish Downtown Lake Eola Retreat

4.88 out of 5 average rating, 40 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. A comfortable green sofa is complemented by accent pillows and paired with a light-colored chair. A wooden coffee table sits centrally, while a flat-screen TV is mounted on the wall.

Flat in Winter Garden

Winter Garden Charm, Near Disney

Flat in Lake Eola Heights

A spacious sleeping area features a large bed with gray bedding, complemented by a decorative mirror on the wall. A small lamp illuminates a side table, while a bookshelf adds to the room's functionality. Soft light filters through a window with wooden blinds.

4.93 out of 5 average rating, 43 reviews

Modern downtown apartment

A compact kitchen area features black cabinetry and a white refrigerator. Stainless steel appliances, including a stove and sink, provide essential amenities. Glassware is visible on the shelves, along with kitchen utensils, ensuring a functional space for meal preparation.

4.97 out of 5 average rating, 30 reviews

Theme Park Treasure Private Apartment

5 out of 5 average rating, 10 reviews

Orlando Best Location, Near Parks, I-Dr & Downtown

5 out of 5 average rating, 12 reviews

Haunted Mansion-inspired Ghoulish Sanctuary

A welcoming living area is furnished with a yellow couch and a light gray armchair, both adorned with decorative pillows. A coffee table with a wooden base displays glass vases. Natural light enters through a partially covered window, and a landscape art piece adds a calming touch.

4.91 out of 5 average rating, 69 reviews

Welcome to The Comfy Cozy Place

Private apartment rentals

A comfortable living area features a light-colored sofa adorned with decorative pillows. A round coffee table sits in front, complemented by a plant centerpiece. Two abstract artworks in gold and blue are displayed on the walls, while a full-length mirror leans against one side.

4.98 out of 5 average rating, 91 reviews

Modern Orlando APT w/Laundry & Private Patio

4.98 out of 5 average rating, 44 reviews

Casa Oliva King Bed Near Parks/Shopping/Food/Golf

4.9 out of 5 average rating, 206 reviews

The bedroom features a spacious bed dressed in soft blue bedding, complemented by two bedside lamps on wooden tables. Decorative curtains with a water-themed design frame the window, while a subtle area rug adds texture to the room's original terrazzo flooring.

Flat in Winter Park

The Lake House

4.97 out of 5 average rating, 288 reviews

A small outdoor table is set for a meal, featuring a chocolate cake topped with strawberries. Around the table, plastic glasses and colorful plates are arranged. Lush greenery surrounds the area, and a view of the lake is visible in the background.

Flat in Winter Garden

Lakeview Garden Studio

A modern living room is depicted with a full sofa, coffee table, and a smart TV. Natural light enters through the sliding glass door leading to the balcony. Three framed botanical prints decorate the wall, while a floor lamp adds soft illumination.

4.98 out of 5 average rating, 57 reviews

Modern Condo: 10 Min to Disney + Fireworks Views!

4.98 out of 5 average rating, 64 reviews

Elegant Budget Friendly Suite. No Resort Fee!

4.83 out of 5 average rating, 18 reviews

Modern Apt w/ Pool, Gym • Near UCF

4.91 out of 5 average rating, 127 reviews

A welcoming living room features a comfortable dark sofa accented by yellow pillows. A wooden coffee table sits in front, complementing the beige rug beneath. A glass desk with a chair is positioned near a window, with natural light illuminating the space. A 'WELCOME HOME' sign adorns the wall.

Flat in College Park

Getaway in comfort with a pool

Apartment rentals with a hot tub

A modern kitchen is highlighted with sleek, white cabinetry and stainless steel appliances. A marble countertop extends into a bar area with three cushioned stools. Glassware sits ready on the counter, complemented by a colorful towel and a decor piece.

4.87 out of 5 average rating, 148 reviews

Just Renovated 2/2 Resort Home

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.

4.85 out of 5 average rating, 168 reviews

BEST Views~2B2B~Universal~Disney

A light-filled living area features a neutral-toned couch adorned with decorative pillows. A natural fiber rug lies beneath, while a dining space with white chairs is seen in the background. Coastal artwork adds a subtle nautical touch to the decor.

4.89 out of 5 average rating, 109 reviews

Beach Heaven minutes from Disney

A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.

4.97 out of 5 average rating, 103 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

A spacious studio is furnished with a large bed and a blue couch. Elegant decor is highlighted by a chandelier above, while a backdrop of a city skyline adorns one wall. Natural light filters through large windows, creating an open and bright atmosphere.

4.89 out of 5 average rating, 365 reviews

Carmen Romantic Studio W/Private Beautiful Terrace

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, 103 reviews

Your condo next to Universal epic universe

An aerial view reveals a sprawling lagoon-style pool surrounded by lush green landscapes, highlighted by winding water features. A well-appointed bedroom presents a spacious bed framed by modern decor and natural light filtering through a window. The living area showcases an elegant dining setup alongside a stylish sofa, while a vibrant children's room features a bunk bed and playful accents.

4.82 out of 5 average rating, 220 reviews

2Bedrooms/2 Bathrooms Storey Lake Resort 3150-404

An inviting living area features a comfortable light-colored couch, a dark wood dining table with four chairs, and rustic decor on the walls. Large windows allow natural light to fill the space, complemented by warm lighting fixtures. A kitchenette with open shelving is visible in the corner.