Apartment holiday rentals in Windermere

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Top-rated apartment rentals in Windermere

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Top guest favourite
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.
Flat in College Park
4.93 out of 5 average rating, 318 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

Top guest favourite
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.
Flat in Kissimmee
4.99 out of 5 average rating, 143 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!

Top guest favourite
A contemporary living area features a large flat-screen TV mounted on a wall. A wooden console table sits beneath it, displaying decorative items. Two upholstered chairs provide seating, with a colorful area rug added for warmth. Natural light filters through window coverings.
Flat in Winter Park
4.96 out of 5 average rating, 224 reviews

Apt C -Modern Elegance in the Heart of Winter Park

Light, bright and full of delight! Fastest internet speed available: 154MBPS download and 20 MBPS upload! Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Heated pool , poolside grill and bikes for your enjoyment! Three blocks to Park Ave and two blocks to the Winter Park Village! Simple elegance downtown defined by contemporary design and leisurely living. Enjoy the convenience and tranquility of one of Florida's best walking communities

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, 144 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
A private balcony is showcased with a round table and two woven chairs, providing a serene view of the lake and surrounding landscape. Soft morning light reflects on the water, while a small potted plant adds a touch of greenery to the setting.
Flat in Orlando
4.97 out of 5 average rating, 101 reviews

2-Bedroom Renovated Lakeside Condo Near Disney

This large lakeside renovated (July 2023) condo is located minutes from all theme parks and is within walking distance to many restaurants and an outlet mall. Enjoy our two main pools (with tiki bar and hot tub) and poolside recliners. Condo includes: large private balcony; laundry; two full bathrooms; master king bed/ensuite; second bedroom with XL twin beds and a bunk bed nook for kids; 55-inch Samsung smart TV in living area and Amazon Fire TVs in each bedroom.

Top guest favourite
A modern living area features a cozy gray sofa draped with a textured throw, complemented by a wooden coffee table. An open kitchen with bar seating is visible, along with neutral walls and tile flooring, providing a spacious and bright environment.
Flat in Clermont
4.98 out of 5 average rating, 100 reviews

Premier Clermont Suite /Prime Downtown 103

Immerse yourself in the sophisticated serenity of our strategically located prime suite, nestled in the vivacious heart of downtown Clermont. elegantly appointed with meticulous attention to detail our suite offers a harmonious blend of opulence and home-like comfort-whichever way you look, every corner is designed to offer an unrivalled stay experience. This property is a dream come true for Triathletes! Standing right at the epicenter of Clermont.

Top guest favourite
A bright and airy living space features a cozy sofa and a circular coffee table surrounded by wooden chairs. Natural light fills the area through a large window adorned with light curtains, while greenery adds a touch of nature to the decor.
Flat in Orlando
4.98 out of 5 average rating, 126 reviews

Top5% *Sunny Oasis* Boho Retreat |FreeParkShuttle

Welcome to Sunny Oasis, your perfect escape in the heart of Orlando. Immerse yourself in a beautifully curated Boho ambiance, filled with natural textures, earthy tones, and sunlit spaces. Whether you’re relaxing after a day at the parks or enjoying a peaceful getaway, Sunny Oasis offers the comfort and serenity you deserve. Book your stay with us and experience the allure of Orlando’s attractions in a clean, serene, and superbly located getaway.

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
4.92 out of 5 average rating, 101 reviews

Penthouse With EPIC Views

A 2024 full remodel by Luiz Durand of the most expensive unit ever sold at The Enclave. Sun rises, a wrap around private terrace and views over 4 theme parks combine to make this a vacation experience unlike any other. Granite and travertine throughout. Stainless steel appliances and oversized smart TVs. Hotel amenities include indoor and outdoor pools, tennis, food court, pub and gym.

Guest favourite
The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.
Flat in Clermont
4.81 out of 5 average rating, 304 reviews

Charming Lakefront Apt. Near Disney

Welcome to our Charming Lakefront Apartment, located in South Clermont, just 20 minutes from Downtown Orlando, Walt Disney World, and all the exciting Central Florida attractions. Nestled on the serene Lake Sawgrass, this peaceful countryside retreat offers fishing, kayaking, boating, and other watersports activities.

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, 112 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.

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
4.9 out of 5 average rating, 165 reviews

Stay A While

Welcome to our secluded away from home. Minutes away to supermarkets, shopping stores, and 25 minutes away from theme parks and nightlife. Approximately 40-minute drive to the Orlando International Airport. We have a dedicated parking area for guests who are traveling with moving trucks, boats, and rv's.

Guest favourite
A comfortable living area is showcased with modern furnishings, including a sectional sofa adorned with colorful accent pillows. A coffee table is positioned on a patterned rug, while large glass doors lead to a balcony offering views of the surrounding area. A wall-mounted television is available for entertainment.
Flat in Orlando
4.8 out of 5 average rating, 175 reviews

Top-Floor Lakeview Condo at Vista Cay Resort

Bright and airy top floor corner unit, conveniently secluded from traffic. This lovely and spacious 3BD/2BA condo is located at The Isles at Vista Cay. The 4th floor location is accessible via two elevators. It's the perfect home for your business trip or your family's next get away to Orlando!

Popular amenities for Windermere apartment rentals

Quick stats about flat rentals in Windermere

  • Nightly prices starting at

    Windermere holiday rentals start at $141 SGD per night before taxes and fees

  • Verified guest reviews

    Over 120 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!

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