Apartment holiday rentals in Winter Park

5 out of 5 average rating, 116 reviews

Private Rooftop Suite! No resort fees! 5 star

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

A spacious studio is showcased with a king-size bed and a queen pull-out sofa. A smart TV is mounted on the wall. A dining table with blue chairs and a small coffee table add functionality to the layout. Soft lighting illuminates the modern decor.

4.81 out of 5 average rating, 146 reviews

NEW Designed Apt 2024 NrUCF PETSOk PrivateEntry

Discover this luxurious, newly renovated Airbnb studio with a FULLY PRIVATE patio featuring a hammock under a shady mango tree. Enjoy PRIVATE LAUNDRY, patio seating, and umbrella. The fenced backyard ensures privacy, minutes from UCF, Universal, Disney, and local amenities. The studio sleeps 4 and is part of a property with a house and a separate private apartment, each with its own kitchen, bathroom, bedroom, sitting room, garden hammock, patio, and entry. Experience tranquility in a quiet area

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.

4.99 out of 5 average rating, 187 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.

Apartment in College Park

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.

4.94 out of 5 average rating, 265 reviews

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

Apartment in Altamonte Springs

A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.

4.96 out of 5 average rating, 337 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

4.91 out of 5 average rating, 181 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.

Apartment 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.

The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.

4.99 out of 5 average rating, 116 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

A well-appointed bedroom is highlighted by a spacious bed with a light-colored quilt. Flanking the bed are two lamps on wooden nightstands. Natural light filters through a large window, adorned with sheer curtains. A decorative mirror and wall art complement the serene atmosphere.

4.95 out of 5 average rating, 123 reviews

Bright & Spotless. Private Apartment

Your Private Orlando Retreat. * (No shared spaces.) * Enjoy complete privacy in your own bedroom, bathroom, living room, kitchen, private entrance, and patio—no shared spaces. * Situated in a quiet, welcoming neighborhood just minutes from Waterford Lakes Town Center’s dining and shopping. * Close to UCF and major highways, offering an easy drive to Orlando’s top attractions, including Disney, Universal, and SeaWorld. Perfect for comfort, convenience, and relaxation.

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.

4.92 out of 5 average rating, 117 reviews

Cozy Zen DT Orlando Apartment - Free Parking

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)

4.97 out of 5 average rating, 198 reviews

The pool area is illuminated at night, showcasing a crystal-clear water pool surrounded by comfortable lounge chairs. Vibrant bougainvillea lines the back wall, adding a pop of color to the tranquil setting. Soft lighting enhances the modern architecture of the adjacent building.

Apartment in Winter Park

Just 3 Blocks to Shops/Restaurants on Park Ave!

Modern, clean and unique. Fast internet speed: 263 MBPS download and 21.5 MBPS upload. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz countertops, high-end cabinetry and fixtures, great new furnishings and mattresses, 8' solid core interior doors, high ceilings, spacious open layout with a balcony offering fantastic sunset views and more! If you haven't explored Winter Park's Park Avenue, then you must!

4.95 out of 5 average rating, 108 reviews

A comfortable living area features a sectional sofa adorned with cushions in shades of yellow, teal, and deep purple. Two small tables sit in front, accompanied by a patterned area rug, while decorative wall art adds visual interest. Natural light filters through a window with blinds.

Apartment in Bay Lake

Charming Oasis 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

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, 196 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.

Popular amenities for Winter Park apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 48 reviews

Stay with Nory and Yuset

Apartment in Thornton Park

An inviting living area is highlighted by a modern white sectional sofa and sleek black armchairs. A large abstract painting adorns the wall. Natural light filters through sliding glass doors that lead to a balcony, illuminating the warm wood flooring.

4.95 out of 5 average rating, 56 reviews

Thornton Park Luxury Loft | Free Prkg | Balcony

A dark wood dresser is positioned against a light grey wall, topped with a potted pink orchid and two matching vases. A mirror reflects the arrangement, while a black lamp stands beside the dresser. Decorative wall art adds a touch of color to the space.

4.91 out of 5 average rating, 22 reviews

Cozy Butterfly House

5 out of 5 average rating, 17 reviews

An open-plan studio layout is displayed, featuring a full kitchen with stainless steel appliances, a dining area with a small table, and a comfortable living space with a dark sofa. A spacious bed is positioned against the far wall, with ample natural light streaming in from multiple windows.

Apartment in Apopka

Comfy Farm Studio Stay

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.

4.99 out of 5 average rating, 75 reviews

Modern Orlando APT w/Laundry & Private Patio

Superhost

A modern dining area features a round glass table surrounded by four black chairs with wooden legs. A minimalist floral artwork hangs on the wall, and sunlight filters through vertical blinds, creating a bright and open atmosphere. A soft area rug adds texture to the floor.

Apartment in Winter Park

5 out of 5 average rating, 3 reviews

Kick off your shoes and Unwind

4.89 out of 5 average rating, 87 reviews

A modern living room features a dark sofa accompanied by two cozy armchairs. A glass coffee table sits in the center, complemented by decorative items. Natural light filters through sheer curtains, illuminating the light-colored flooring and minimalist decor.

Apartment in Metro West

Escape to Orlando near Universal Studios.

5 out of 5 average rating, 22 reviews

Beautiful and Romantic Private Suite

Private apartment rentals

4.96 out of 5 average rating, 23 reviews

An open living area is visible, featuring a large black sectional sofa and a contemporary coffee table. A wall-mounted TV and stylish decor enhance the space. A small dining area with bar stools and a kitchen counter is included, along with a decorative plant for added life.

Apartment in Ventura

2 Bed 2 Bath Golf Resort Condo (2ND FL)

4.95 out of 5 average rating, 22 reviews

*NEW* Villa Amalfi Boho• FreeParksShuttle•PoolView

A modern living area features a sectional sofa adorned with decorative pillows and a coffee table at the center. A large wall-mounted television provides entertainment options, while expansive glass doors open to a balcony showcasing scenic views. Bright lighting enhances the open and airy ambiance.

4.95 out of 5 average rating, 64 reviews

3191-307 Resort Lake View Disney Universal Orlando

An open living space is presented, featuring a spacious sofa with decorative pillows and a coffee table. A wall-mounted television is positioned above a low media console. The kitchen area includes bar seating and modern appliances, with light flooding in from a nearby window.

5 out of 5 average rating, 13 reviews

Brand New Lakeside Retreat Apartment

Superhost

A cozy bedroom features a spacious bed with dark bedding and a gray throw blanket placed on top. A side table with a lamp is positioned beside the bed. A black curtain covers the window, and a large palm tree photograph decorates the wall above the bed.

Apartment in Altamonte Springs

4.8 out of 5 average rating, 50 reviews

Apartment in Altamonte Springs!

A spacious living area is presented with a comfortable sofa adorned with decorative pillows. A coffee table sits center, displaying a small vase of flowers. A dining table with six chairs is positioned to the left, complemented by soft lighting from two lamps.

5 out of 5 average rating, 24 reviews

Spacious & Cozy Orlando APT Near Disney Parks!

A well-maintained outdoor area features a sparkling pool surrounded by lounge chairs. A bar with shaded seating stands nearby, framed by palm trees and manicured landscaping. The building in the background includes balconies, allowing for a relaxed atmosphere.

4.93 out of 5 average rating, 57 reviews

Premier Resort Condo Suite Near Universal & Disney

Superhost

A charming entrance is highlighted by double doors framed by potted plants and seasonal decorations. The red exterior is complemented by a white porch, while two whimsical figures stand on either side of the door, creating an inviting focal point.

Apartment in Eatonville

4.67 out of 5 average rating, 30 reviews

Cozy Town Suites A

Apartment rentals with a hot tub

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, 86 reviews

Penthouse With EPIC Views

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.

4.83 out of 5 average rating, 147 reviews

BEST Views~2B2B~Universal~Disney

Apartment in CHAMPIONS GT

A contemporary bedroom features a spacious bed with a blue throw blanket and decorative pillows. A tufted blue headboard adds style, while sunlight streams through a large window adorned with patterned curtains. A circular mirror and bedside lamps enhance the modern decor.

4.89 out of 5 average rating, 218 reviews

Magical Newly Renovated 10 minutes to Disney 2+2

4.93 out of 5 average rating, 402 reviews

Completely Reno 3/2 near Disney & Universal parks

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.

4.88 out of 5 average rating, 344 reviews

Carmen Romantic Studio W/Private Beautiful Terrace

A bright living area features a light-colored couch with decorative cushions, a patterned armchair, and a wooden coffee table. Natural light enters through large windows adorned with blinds. A ceiling fan hovers above, and a potted plant adds a touch of greenery.

4.9 out of 5 average rating, 151 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

The bedroom features a spacious bed dressed in white linens, complemented by a decorative pillow. Artwork of iconic characters adorns the wall above the headboard. A lounge chair is positioned beside a window, with blackout curtains surrounding the space.

4.89 out of 5 average rating, 105 reviews

King Bed/Free Shuttle to all Parks/Pool & Hot Tub

A modern living area features a cozy sofa and dining table, with a kitchenette visible in the background. A desk is positioned beside the doorway. A spacious sleeping area can be seen through an open entryway, showcasing a king-size bed and additional seating.