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Apartment holiday rentals in Windermere

Find and book unique apartments on Airbnb

Quick stats about flat rentals in Windermere

  • Nightly prices starting at

    Windermere holiday rentals start at $142 SGD per night before taxes and fees

  • Verified guest reviews

    Over 130 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
A resort-style pool area features a spacious swimming pool surrounded by lounge chairs. The building offers large windows and a welcoming entrance, complemented by palm trees and tropical landscaping. Umbrellas provide shade over the seating, creating a relaxing outdoor retreat.
Flat in Windermere
4.96 out of 5 average rating, 56 reviews

Pool, Gym, Parking Access - Lakeside Haven Stay

Located in Windermere, our Waterfront Retreat combines suburban tranquility with proximity to Orlando's buzz. This quiet getaway offers serene lake views around the property, a private balcony, modern comforts in a cozy queen bedroom with a smart TV, and a kitchen equipped with a dishwasher for your culinary exploits. Enjoy added conveniences like in-unit laundry and exclusive access to a resort-style pool and gym. Perfect for those looking for a peaceful escape near the city's top attractions.

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.
Flat in Winter Garden
4.96 out of 5 average rating, 56 reviews

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.

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.
Flat in Orlando
4.93 out of 5 average rating, 116 reviews

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.

Top guest favourite
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
4.97 out of 5 average rating, 155 reviews

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.

Top guest favourite
Flat in Kissimmee
4.96 out of 5 average rating, 209 reviews

Top1% *La Piu Belle* Retreat at Storey Lake View

Welcome to **La Piu Belle Retreat** – a stylish, sunny, and serene escape at Storey Lake Resort. This 2-bedroom condo features boho-chic decor, a fully equipped kitchen, a bright balcony, and cozy vibes throughout. Enjoy access to a water park, gym, and more. Perfectly located just minutes from Disney, premium outlets, and top restaurants. Excellent Reviews: Our guests rave about their experiences, highlighting our cleanliness, location, and exceptional service.

Guest favourite
A spacious living area features a sectional sofa and a round coffee table, complemented by soft lighting. A television is placed on a low cabinet, while decorative plants and a wall art piece add visual interest. Natural light enters through a window, enhancing the inviting atmosphere.
Flat in Winter Garden
4.89 out of 5 average rating, 169 reviews

Stay A While

Welcome to Your Secluded Getaway 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

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.
Flat in Clermont
4.99 out of 5 average rating, 144 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.

Guest favourite
A living room is presented with green accent walls and hardwood flooring. A comfortable sofa with orange throw pillows faces two small coffee tables. Wall decorations include woven art pieces. A ceiling fan hangs above, and a door leads to a balcony, allowing natural light into the space.
Flat in Kissimmee
4.93 out of 5 average rating, 176 reviews

Cozy 2Bed Boho Hideaway 10 Min to Parks Allows Pet

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 8 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Guest favourite
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.
Flat in Orlando
4.88 out of 5 average rating, 211 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.

Top guest favourite
Flat in Doctor Phillips
4.99 out of 5 average rating, 303 reviews

Studio Apartment attached to House.

2 King Sized Beds. 1 Bathroom. Sleeps 4. Studio Apartment mother-in-law suite 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. Disney World is 6 miles or less than 30 minutes away & Universal Studios is 2 miles or 5-10 minutes away. Coffee, tea, cream & sugar are included. Self Check in by digital key pad. Free parking on site.

Top guest favourite
The living area features a light-colored sofa and two patterned armchairs arranged around a small coffee table. Natural light fills the space through multiple windows, with a television placed on a dark wood console. Framed artwork adorns the walls, adding visual interest.
Flat in Windermere
4.99 out of 5 average rating, 116 reviews

Relaxing 2BR Lakeview Retreat Close to Attractions

Relaxing getaway with gorgeous lake views in historic Windermere just minutes from Disney, Universal, and all Orlando-area attractions. Skip the tourist traps and retreat to this charming, newly renovated apartment in quiet, old Florida. Perfect for families visiting the parks or anyone seeking a quiet getaway.

Top guest favourite
A silhouette of a crane stands at the lake's edge against a vibrant sunset. The sun casts a warm orange and yellow glow over the water, creating a peaceful backdrop. The surrounding foliage is subtly outlined by the light reflecting on the surface.
Flat in St. Cloud
4.96 out of 5 average rating, 502 reviews

LAKE FRONT Apartment w FREE Kayaking/Canoe

Cozy, secluded lake front apartment with private entrance. Newly renovated 1 bd with kitchenette, bathroom and private Lanai. Free use of Kayaks and canoes that can be easily launched from our private canal. ***ADULT guests only***

Popular amenities for Windermere apartment rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Windermere
  6. Flat rentals