Apartment holiday rentals in Winter Park

4.98 out of 5 average rating, 127 reviews

Private Rooftop Suite! No resort fees!

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.

The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.

4.98 out of 5 average rating, 161 reviews

3121-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

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, 155 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, 198 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.

4.93 out of 5 average rating, 281 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

4.91 out of 5 average rating, 191 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.

A cozy sleeping area features a queen-size bed with a light textured coverlet. Green accent pillows add a splash of color. Shelves above display decorative items, while a bedside table holds a clock. Natural light filters through a window, enhancing the inviting ambiance.

4.92 out of 5 average rating, 368 reviews

“The Velvet Escape” Near Attractions & Airport

Get ready to enjoy your vacation in this chic and comfortable apartment in the heart of Orlando. Located directly in front of the Florida Mall, this home is a convenient 15-20 min drive from all the major attractions. This is a private apartment, with it's own free parking and fenced in patio. The open layout, with private full kitchen and private bathroom makes it perfect for couples, solo adventurers, and business travelers. The stay includes FREE wifi, Netflix, and full stocked kitchen

Apartment in College Park

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.

4.91 out of 5 average rating, 124 reviews

Getaway in comfort with a pool

This excellent apartment has been furnished to a great standard. It’s the ideal retreat for a laid back & up-scale stay, located close to the absolute heart of Orlando. The neighborhood is known for its 20th-century cottages, abundant green spaces and lakes. Get ready to get inspired! Very close to some fabulous sites. All in all, guaranteed enjoyment and relaxation. All-day long. Settle in by zoning out with the four of you in a professionally cleaned home.

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, 123 reviews

DT Orlando 1/1 Sunset View - 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)

Apartment in Lake Eola Heights

4.8 out of 5 average rating, 102 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, 199 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.

4.89 out of 5 average rating, 178 reviews

Apartment, 7 Min to Orlando Airport/ Lake Nona

Complete private unit . A Private Door inside the room to step out to the pool .1 Bed/1 Bath, Pool area will be available all the time .We just build a door inside the room that way is easy access. This place is 25 Minutes driving to Disney World and most Parks, Lake Nona is 10 minutes away. We are Close to UCF, lake Nona, MCO, Waterford lakes

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, 67 reviews

Stay with Nory and Yuset

4.96 out of 5 average rating, 28 reviews

*NEW* Villa Amalfi Boho• FreeParksShuttle•PoolView

4.88 out of 5 average rating, 40 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.

Apartment in South Eola

Stylish getaway on Lake Eola

Apartment 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, 40 reviews

Modern downtown apartment

4.75 out of 5 average rating, 16 reviews

Modern Studio Next to Disney & Universal!

5 out of 5 average rating, 36 reviews

Yania's Cozy Getaway

The living area features a spacious gray sectional sofa arranged around a white coffee table, with decorative items adding style. A large window provides natural light, complemented by modern shelving and a lamp. The open kitchen is visible in the background, emphasizing a comfortable layout.

5 out of 5 average rating, 66 reviews

Modern Luxury Kissimmee Retreat

4.89 out of 5 average rating, 89 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.

Private apartment rentals

A spacious living area showcases a gray sofa adorned with decorative pillows. A dark rug sits beneath the seating arrangement, while a dining set with light wooden chairs and a round table is visible in the adjacent open-concept kitchen. A ceiling fan and floor lamp provide ambient lighting.

4.87 out of 5 average rating, 91 reviews

Relax in Cozy Apt 1/1 near to Disney

5 out of 5 average rating, 6 reviews

Modern Vacation Home Just Minutes from Disney 8

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.

4.93 out of 5 average rating, 27 reviews

Cozy Butterfly House

4.91 out of 5 average rating, 23 reviews

Apartment in Davenport

3-Bedroom Getaway!

5 out of 5 average rating, 11 reviews

Studio # 5 One bed, one sofa bed, no smoking 4 people

Apartment in Altamonte Springs

5 out of 5 average rating, 7 reviews

The Noir Getaway

A cozy balcony is furnished with a comfortable seating area, featuring a blue sofa and a light-colored table. Palm trees are visible in the foreground, along with a serene waterfront view that stretches into the distance under a clear blue sky.

4.99 out of 5 average rating, 97 reviews

Lake View Penthouse

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.

4.94 out of 5 average rating, 65 reviews

Premier Resort Condo Suite Near Universal & Disney

Apartment rentals with a hot tub

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, 155 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, 220 reviews

Magical Newly Renovated 10 minutes to Disney 2+2

A sparkling pool is set in a sunny courtyard, surrounded by palm trees and lounge chairs. The three-story building features yellow exterior with red-tiled roofs, and a secure fence encloses the area for privacy and safety.

4.93 out of 5 average rating, 118 reviews

2 bedrooms 2 baths near Disney Universal Seaworld

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.

4.79 out of 5 average rating, 380 reviews

Westgate Lakes+Spa Studio Sleeps 4

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, 352 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.

4.89 out of 5 average rating, 158 reviews

Modern 3 Bedroom Apartment Near the Theme Parks

A sunlit living area is shown with a gray sofa and a white coffee table in the center. A large window reveals a view of greenery outside, while a mounted flat-screen TV is visible on the wall. A bedroom is glimpsed through an open door.

4.81 out of 5 average rating, 109 reviews

Suites at Lake Buena Vista close Disney Springs A8

The open living area features a comfortable seating arrangement with dark leather couches and accent chairs. A wooden coffee table sits in the center, while large windows allow natural light to flood the space. A dining area is included, enhancing the inviting setting.