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Apartment vacation rentals in Windermere

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Quick stats about apartment rentals in Windermere

  • Nightly prices starting at

    Windermere vacation rentals start at $155 CAD per night before taxes and fees

  • Verified guest reviews

    Over 140 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windermere rentals

  • 4.9 Average rating

    Windermere stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated apartment rentals in Windermere

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

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Guest favourite
Apartment 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

ValueFamilyCondition

4.89 out of 5 average rating, 169 reviews
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

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.

LocationValueCheck-in

4.92 out of 5 average rating, 118 reviews
Top guest favourite
Apartment in Doctor Phillips

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 : )

ValueFamilyNearby

4.99 out of 5 average rating, 315 reviews
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

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

LocationFamilyParking

4.89 out of 5 average rating, 105 reviews
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

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!

FamilyValueOutdoor spaces

4.84 out of 5 average rating, 181 reviews
Top guest favourite
A stylish living area features a large, gray sectional sofa accompanied by two teal chairs. A coffee table with decorative items is centered on a soft area rug. Natural light enters through two large windows, complemented by flowing curtains. A wall adorned with tropical leaves adds a vibrant touch.
Apartment in Winter Garden

Emerald Grove - Close to 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 steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

LocationFamilyGetting around

4.97 out of 5 average rating, 62 reviews
Top guest favourite
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.
Apartment in Orlando

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.

FamilyValueParks

4.94 out of 5 average rating, 127 reviews
Top guest favourite
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.
Apartment in Orlando

Wizard-Themed Condo Near Universal

Make some magical memories at this one-of-a-kind, intensely themed condo for witches and wizards of all ages, located just blocks away from Universal Studios and Universal Islands of Adventure. Between forays into the parks, relax at the pool and hot tub, grill up some savory delights, play basketball, or tone your abs in the gym. Then deepen your adventures with the large TV's, Playstation with Hogwarts Legacy, and other Harry Potter games.

FamilyLocationKitchen

4.95 out of 5 average rating, 143 reviews
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

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!

FamilyLocationGetting around

4.93 out of 5 average rating, 162 reviews
Guest favourite
A cozy sleeping area features a tufted headboard and a well-made bed with crisp white linens. A nightstand with a lamp and decorative vase sits beside the bed. A tray holds two glasses and a floral arrangement, adding a touch of charm to the space.
Apartment in Orlando

Cozy Suite next to Universal/I Drive

You will love to stay at our cozy studio located in the best place of Orlando, near to all the fun and entertainment. Just minutes away from Universal Studios, Icon Park, Sea World, Disney, Volcano Bay and plenty of outlets, restaurants, gift shops , grocerie stores. The studio has a Queen bed a Sofabed with a Tv 55 inches, nice view to the pool and a kitchenette with all you need to enjoy a simple meal.

LocationValueCheckout

4.91 out of 5 average rating, 106 reviews
Top guest favourite
Apartment in Orlando

Luxury 1BR & Resort Amenities - 6min to Epic-Uni

Welcome to our Modern 1-Bedroom, 1-Bathroom Apartment in the heart of Orlando, FL! This stylish and cozy apartment is the perfect home base for your Florida getaway, offering a relaxing atmosphere and convenient access to nearby theme parks, shopping, and dining. Enjoy resort-style amenities and a comfortable stay in the center of Orlando. Please reach out for any potential multi-day discounts available

LocationParkingParks

5.0 out of 5 average rating, 18 reviews
Superhost
A cluster of multi-story buildings is set against a clear blue sky, reflected in the calm waters below. Lush green palm trees and vibrant landscaping add to the serene atmosphere surrounding the resort.
Apartment in Orlando

Westgate Lakes + Spa 1 Bed Deluxe Sleeps 4

Offering a one bedroom deluxe apartment at Westgate Lakes Resort & Spa with a King Bed, Sofa Bed and full kitchen and balcony. Ideally located close to the Orlando area attractions and with amazing on site amenities Westgate Lakes & Spa is a fabulous place to stay. A great location to visit the local attractions

ValueFamilyBathroom

4.89 out of 5 average rating, 117 reviews

Popular amenities for Windermere apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favourite
Apartment in Orlando

Orlando Bliss near Disney

LocationFamilyLaundry

5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Orlando

Epic stay at Vista Cay!

LocationValueQuiet

4.95 out of 5 average rating, 60 reviews
Guest favourite
Apartment in Doctor Phillips

New 1 Bedroom Suite with full kitchen bathroom #1

LocationFamilyNearby

4.84 out of 5 average rating, 25 reviews
Guest favourite
Apartment in Orlando

Top1| Villa MontBlanc BohoLuxe|OrlandoEyeView&Pool

LocationViewHospitality

5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Kissimmee

Haunted Mansion-inspired Ghoulish Sanctuary

FamilyValueAccess

4.98 out of 5 average rating, 40 reviews
Guest favourite
Apartment in Orlando

Lakeside Retreat | Minutes from Universal & Disney

LocationParksKitchen

5.0 out of 5 average rating, 12 reviews
Guest favourite
Apartment in Kissimmee

Brand new luxury near clubhouse / lake view (405)

FamilyLocationCheckout

4.9 out of 5 average rating, 21 reviews
Superhost
Apartment in Kissimmee

Luxury Reunion Retreat Patio Views Near Disney

LocationHospitalityComfort

5.0 out of 5 average rating, 3 reviews

Private apartment rentals

Guest favourite
Apartment in Orlando

VC0-304 - 4BR apartment near universal with hot

LocationCleanlinessHot tub

5.0 out of 5 average rating, 5 reviews
Superhost
Apartment in Orlando

Mills 50 1BR | Sleeps 4 | Workspace | Free Parking

LocationValueNearby

5.0 out of 5 average rating, 7 reviews
Top guest favourite
The living area is furnished with a cozy blue sofa and a colorful area rug, providing a vibrant contrast against a blue accent wall. A dining table is visible in the background, alongside modern kitchen appliances. Natural light illuminates the space, creating an inviting atmosphere.
Apartment in Kissimmee

King Bed Apartment, Close to Disney

ValueFamilyComfort

4.95 out of 5 average rating, 94 reviews
Top guest favourite
Apartment in Orlando

Rocio's lovely space.

ValueLocationCleanliness

4.96 out of 5 average rating, 45 reviews
Top guest favourite
A resort-style pool area is surrounded by palm trees, featuring a large swimming pool and a separate hot tub. Multiple lounge chairs are arranged around the pool deck, and the exterior of the building provides a colorful backdrop with balconies overlooking the area.
Apartment in Orlando

Universal - Disney Dream 1 Bedroom-The Point 606S

ValueFamilyGetting around

4.95 out of 5 average rating, 42 reviews
Top guest favourite
Apartment in Kissimmee

Modern Condo: 10 Min to Disney + Fireworks Views!

FamilyValueView

4.96 out of 5 average rating, 74 reviews
Guest favourite
Apartment in Orlando

Luxury 2BR Suite l Downtown, Pool, Gym, Games!

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in Kissimmee

8050-112 Luxury 2BR Apt Kissimmee Orlando Disney

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 17 reviews

Apartment rentals with a hot tub

Guest favourite
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.
Apartment in Orlando

Just Renovated 2/2 Resort Home

ValueFamilyGetting around

4.88 out of 5 average rating, 160 reviews
Guest favourite
A cozy studio features a stylish dining area with a round glass table and two blue velvet chairs. A comfortable sofa and bed are accompanied by decorative pillows. The backdrop showcases a city skyline mural illuminated at night, adding visual interest to the space.
Apartment in Orlando

Cozy studio at The Enclave Hotel & Suites Orlando

FamilyValueWalkability

4.7 out of 5 average rating, 287 reviews
Guest favourite
A welcoming outdoor space is surrounded by tall palm trees and modern apartment buildings. Comfortable seating arrangements in turquoise create a relaxed atmosphere. A barbecue area and a well-defined pathway enhance the communal area, inviting social gatherings.
Apartment in Orlando

Resort Studio Near Universal

LocationFamilyHospitality

4.89 out of 5 average rating, 105 reviews
Top guest favourite
An inviting living area features a dark sofa adorned with colorful cushions, alongside a round coffee table. A stylish light fixture illuminates the space, while a patterned rug adds warmth. The dining area is visible in the background, fostering a cohesive atmosphere.
Apartment in Orlando

The best view inside and out.

LocationValueLaundry

4.93 out of 5 average rating, 267 reviews
Guest favourite
Apartment in Orlando

King Bed/Free Shuttle/Kitchen/Pool/Hot Tub/Kitchen

ValueFamilyParking

4.91 out of 5 average rating, 129 reviews
Guest favourite
The open-plan living area features large windows offering expansive views of the water and surrounding landscape. A dining table accommodates six, while a comfortable seating area is arranged for relaxation. Natural light fills the space, enhancing the modern decor.
Apartment in Orlando

Spectacular 2B Condo Disney/Lake views 2 Balconies

LocationFamilyLayout

4.93 out of 5 average rating, 130 reviews
Guest favourite
A patio area is shown with several blue lounge chairs arranged around a landscaped space. In the background, a lagoon features a fountain, while palm trees and a clubhouse enhance the view under a partly cloudy sky.
Apartment in Kissimmee

Runaway Beach Club: Spacious Condo Near Disney!

FamilyValueCheckout

4.91 out of 5 average rating, 100 reviews
Superhost
An inviting pool area is surrounded by lush palm trees and tropical landscaping. Lounge chairs and shaded umbrellas offer comfortable seating options. The pool is centrally located within a gated space, with buildings flanking either side, enhancing the community feel of the environment.
Apartment in Kissimmee

Modern Pool View Villa near Disney & Parks

ValueFamilyWifi

4.83 out of 5 average rating, 461 reviews

Destinations to explore