Apartment holiday rentals in Winter Garden

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Quick stats about apartment rentals in Winter Garden

Total holiday rentals
Explore 20 holiday rentals in Winter Garden
Nightly prices starting at
Winter Garden holiday rentals start at $68 NZD per night before taxes and fees
Verified guest reviews
Over 320 verified reviews to help you choose
Pet-friendly accommodation
Find 10 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 of Winter Garden holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Garden rentals
4.8 Average rating
Winter Garden stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated apartment rentals in Winter Garden

Guests agree: These apartments are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Winter Garden

4.89 out of 5 average rating, 169 reviews

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

ValueFamilyQuiet

Top Guest favourite

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.

Apartment in Orlando

4.94 out of 5 average rating, 115 reviews

Your condo next to Universal epic universe

This 1247 sq/ft condominium is part of Vista Cay Orlando Fl. I keep my condo clean and in excellent condition for all of my guests. The condominium is centrally located within the entertainment and attractions district of Orlando, only minutes from International drive ,Sea World the Orange county convention center and just 9 minutes from Universal and 15 minutes from Disney. You'll have quick access to great restaurants shops and many local attractions.We just opened up a new pool its beautiful.

ValueFamilyTV

Guest favourite

Apartment in Winter Garden

5.0 out of 5 average rating, 7 reviews

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.

LocationAccuracyCleanliness

Superhost

A modern living space features a large television mounted on a bright wall, adorned with vibrant floral artwork. A cozy gray sofa is accompanied by a coffee table on lush green carpet, while a dining table for four is set against a well-equipped kitchen backdrop.

Apartment in Winter Garden

4.88 out of 5 average rating, 104 reviews

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

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Top Guest favourite

Apartment in Doctor Phillips

4.99 out of 5 average rating, 312 reviews

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 : )

ValueFamilyParking

Superhost

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.

Apartment in Orlando

4.84 out of 5 average rating, 180 reviews

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!

FamilyLocationTV

Guest favourite

Aerial view of the pool area shows vibrant water slides winding through landscaped surroundings. Multiple swimming pools can be seen, complemented by palm trees and open spaces. Sun loungers are arranged around the pools, offering ample relaxation spots for guests.

Apartment in Kissimmee

4.9 out of 5 average rating, 107 reviews

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

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Superhost

Apartment in Horizon West

4.86 out of 5 average rating, 43 reviews

Upstay: Stylish Resort Getaway w/ Pool near Disney

Welcome to your home away from home in the heart of Palisades Condominiums—a well-loved community blending both short and long-term stays. This stylish three-bedroom condo offers the perfect balance of comfort, convenience, and resort-style living. Ideal for small families or a getaway with friends, the space is thoughtfully designed for relaxation and connection. You’re just a 10-minute drive from the magic, making this an unbeatable location for your Orlando adventures.

ValueFamilyHot tub

Top Guest favourite

A modern living area features a vibrant red sofa and two gray armchairs, offering ample seating. A stylish coffee table sits centrally, complemented by a small plant centerpiece. A large television is positioned opposite the seating, with soft lighting from table lamps creating a welcoming ambiance.

Apartment in Clermont

4.98 out of 5 average rating, 154 reviews

Modern Suite in the Heart of Downtown Clermont 101

Experience luxury and excitement in our chic modern suite nestled in the vibrant heart of downtown Clermont. Perfectly poised for Triathletes, this suite is a beacon of comfort and convenience, mere steps away from charming downtown boutiques, delightful restaurants and local breweries. The location is unparalleled with close proximity to the celebrated Clermont/Minneola Trail, esteemed host of prestigious Triathlons and the serene Waterfront Park.

LocationFamilyComfort

Guest favourite

Apartment in Meadow Woods

4.97 out of 5 average rating, 100 reviews

Pet-Friendly | King Bed | Gym & Pool | Near Parks

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.

LocationFamilyView

Guest favourite

A spacious sleeping area features a large bed centered on a neutral carpet. A light area rug is placed beneath the bed. Simple furniture includes a white table and two chairs, along with a TV stand. Natural light filters through sheer curtains.

Apartment in Ocoee

4.92 out of 5 average rating, 159 reviews

Cozy Private Suite w/Bath and Private Entry

Peaceful, and Centrally-located Master Suite with Private Entry, oversized Private Bathroom (toiletries included), and Kitchenette with all of the necessities to make a nice meal! Located just a short drive to Downtown, Theme Parks, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for a short or long term stay. Special accommodations available upon request. Come bask in the Florida Sun!

LocationFamilyCondition

Top Guest favourite

A dining table is set for six, adorned with teal plates and drinking glasses. The living area features a comfortable gray sofa and a TV mounted on the wall, with natural light filtering in from the balcony doors, which lead to a green outdoor seating area.

Apartment in Kissimmee

4.94 out of 5 average rating, 424 reviews

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.

ValueLocationKitchen