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Vacation rentals in Windermere

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Quick stats about vacation rentals in Windermere

  • Nightly prices starting at

    Windermere vacation rentals start at R 1,132 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 250 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 vacation rentals in Windermere

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

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Top guest favorite
A bright living area features two rattan chairs positioned on a decorative area rug. Framed artwork adorns the wall behind the chairs. A dining area is visible in the background, with a modern table and pendant lighting, creating a welcoming space.
Home in Winter Garden

Downtown Bungalow with fire pit and putting green

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

4.97 out of 5 average rating, 133 reviews
Guest favorite
A comfortable living room features a large flat-screen TV positioned on a white media console. Two sofas, one light beige with patterns and one in a solid color, surround a coffee table, with a ceiling fan overhead and colorful curtains framing the windows.
Home in Orlando

10 Minutes to Universal - Charming Private Home

Beautiful newly remodeled home centrally located. 3 bedrooms (2 King 1 Queen) and 2 full baths (1 walk in shower w/ grab bars). Carport. Huge and private yard to enjoy! Comfortable living room with big screen TV, couches and lazyboy recliners. Kitchen is fully stocked for cooking. Office desk and chair. Washer and Dryer. 10 Minutes to Universal Studios and just minutes more to International Drive, Mall of Millenia, Florida Mall, or Disney. Grocery, liquor, pizza, chinese within a 5 minute walk.

4.95 out of 5 average rating, 342 reviews
Top guest favorite
An exterior view of the guesthouse displays a quaint two-story structure with a black garage and a welcoming front porch. Surrounding greenery provides a natural setting, enhancing the privacy of the location. The two upper windows are adorned with large curtains.
Guesthouse in Ocoee

NEW 1BRM Guesthouse | King Bed | Central Florida

Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

5.0 out of 5 average rating, 151 reviews
Top guest favorite
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 : )

4.99 out of 5 average rating, 315 reviews
Superhost
A mid-century home is framed by mature oak trees, providing shade to the grassy front yard. Large windows reflect the natural light, highlighting the clean lines of the exterior. The tranquil setting is complemented by the beauty of the surrounding landscape.
Home in Windermere

Water Front Haven

Skip the crowds and experience the true Florida lifestyle. Beautiful home on a safe, quiet street with access to 12 lakes in your back yard. Simple & clean decor. Outdoor dining on porch & dock. Close to attractions & beaches (45 min). Nestled among palm, oak & camphor trees. Feed the fish and turtles from your private dock. Rent a boat and explore lovely lakes. Enjoy nightly walks on sandy streets canopied by old oak trees. Walk to parks, coffee shops, cafes and swimming areas.

4.93 out of 5 average rating, 28 reviews
Guest favorite
Home in Orlando

Key West Themed Lakefront Oasis with Sailboat

Please read the entire description before booking (including "policies and rules"). This is the lower half of a large lakehouse. Enjoy a resort-like experience with a private pool, heated spa, and stunning sunsets. With a fun Key West theme, it comfortably sleeps your group and features a separate entrance for complete privacy. Enjoy an outdoor kitchen, fire pit, and even a sailboat for a unique stay. Perfect for families seeking a memorable getaway. Kayaks are included for you to explore.

4.89 out of 5 average rating, 106 reviews
Superhost
Home in Winter Garden

Downtown Winter Garden Luxury Retreat (NO Parties)

Welcome to your private luxury escape in Downtown Winter Garden! This recently renovated 3BR/1BA gated home offers comfort, style, and convenience just minutes from Disney, Universal, and major highways. Stroll or drive 1 min to farmers markets, trails, and top restaurants. Enjoy a lush backyard oasis with outdoor dining, cooking space, mini golf, and a cozy hangout area. Perfect for up to 6 guests. STRICT NO PARTY POLICY. 6 GUESTS ONLY DOUBLE RESERVATION CHARGE FOR PARTIES. Pet fee $150

4.9 out of 5 average rating, 29 reviews
Guest favorite
A small, white house is framed by vibrant greenery and colorful plants. The front door, painted blue, adds a pop of color, while large windows allow light to fill the space. A wooden deck leads up to the entrance, enhancing the welcoming appeal.
Home in Winter Garden

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

4.92 out of 5 average rating, 226 reviews
Top guest favorite
The exterior of a renovated cottage is showcased, featuring a welcoming front porch with two wooden chairs. Potted plants are placed on the porch and along the walkway, while a wooden fence stands in the background, enhancing privacy.
Cottage in Winter Garden

The Heart of Winter Garden: Walk to shops & dining

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

4.99 out of 5 average rating, 199 reviews
Guest favorite
Guesthouse in Windermere

Great location, sound of nature

Welcome to your peaceful retreat in a prime location. This minimalist yet fully equipped home accommodates up to 5 guests and features 3 comfortable bedrooms and 2 full bathrooms. Perfect for families, friends, or business travelers. The backyard is fully yours – and pet-friendly! You’ll find everything you need, if something’s missing, we’re just a message away. Whether you're here for fun, work, or rest, this home offers a comfortable and accessible base for your Orlando adventures.

4.86 out of 5 average rating, 7 reviews
Top guest favorite
A living area features a plush sofa and two armchairs arranged around a circular coffee table. Natural light filters through the window, illuminating the space. A vibrant area rug anchors the seating area, while a bouquet of flowers adds a touch of color on the table.
Home in Winter Garden

Downtown Winter Garden, Florida

Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

4.99 out of 5 average rating, 161 reviews
Guest favorite
A modern living area features two comfortable sofas, a wooden coffee table, and a vibrant green plant. A sleek television is mounted on the wall, while the open kitchen area showcases contemporary cabinetry and a light backsplash. Natural light flows in through large windows.
Home in Orlando

The Lake House - Next to Universal Studios - NEW ♥️

Luxurious, modern and completely remodeled single-family home with lake access in the prestigious Doctor Phillips neighborhood. Centrally located hops away from all Orlando has to offer, 1.1 miles (3 minutes) from Universal Studios Theme Parks, 9.5 miles to Disney World and 5 miles to Seaworld Orlando. No other Airbnb offers this upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

4.95 out of 5 average rating, 288 reviews

Popular amenities for Windermere vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Windermere

Guest favorite
An open living space features a plush gray couch adorned with light-toned throw blankets. A wooden coffee table sits nearby, complemented by decorative items. Large windows allow natural light to enhance the room's bright ambiance.
Home in Winter Garden

Cozy cottage in Winter Garden

4.97 out of 5 average rating, 66 reviews
Top guest favorite
The exterior of the home features a covered porch with seating, overlooking a sandy beach area and a clear lake. Two kayaks are positioned on the shoreline, with a grassy area leading to the water's edge. The surrounding landscape includes residential properties and trees in the background.
Home in Ocoee

Lakefront in West Orlando Florida

4.92 out of 5 average rating, 98 reviews
Guest favorite
Apartment in Windermere

Poolside single apartment

4.87 out of 5 average rating, 30 reviews
Guest favorite
Home in Winter Garden

Winter Garden Butterfly Retreat - Trailside

4.97 out of 5 average rating, 34 reviews
Top guest favorite
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

4.97 out of 5 average rating, 62 reviews
Guest favorite
A white-bricked fireplace is positioned against a sleek wall, complemented by a dark wooden mantel. Decorative figures atop the mantel add interest, while a potted plant sits on the floor beside the fireplace, enhancing the inviting atmosphere.
Home in Gotha

The Cute House

4.95 out of 5 average rating, 37 reviews
Guest favorite
A well-lit bedroom features a spacious bed adorned with a patterned blanket. The walls are painted in calming shades of blue, complemented by bright yellow accents. Two decorative plants are positioned on either side of the bed, while a window allows natural light to fill the room.
Home in Winter Garden

Your Enchanted Villa Near Downtown Winter Garden

4.93 out of 5 average rating, 14 reviews
Guest favorite
Condo in Horizon West

2BR Modern Pet-Friendly Condo 6 mins from Disney

4.91 out of 5 average rating, 86 reviews

Frequently Asked Questions

  • What are the best places to stay in Windermere?

    Stays near the lakes, the historic town center, or tree-lined neighborhoods are frequently suggested for a relaxing visit. These areas combine tranquil surroundings with easy access to parks and local shops.

  • What are the best things to do in Windermere with kids?

    Families often explore local playgrounds, community parks, and scenic lake areas that invite paddleboarding or fishing. Around Windermere, interactive museums and wildlife encounters add hands-on fun for kids.

  • What are some of the best things to do in Windermere?

    Explore the lakes by paddleboard or kayak, visit local markets, and stroll the tree-lined historic town center. The area also has art spaces, community parks, and coffee shops for a laid-back day.

  • How is the weather in Windermere?

    Windermere has warm, humid summers around 91°F (33°C) at their peak, with winters that are typically mild, rarely dipping below 49°F (10°C). Expect more rain in the summer months, and pack light layers and a rain jacket year-round.

  • When is the best time to visit Windermere?

    Late fall through early spring is frequently suggested for visiting Windermere, thanks to milder temperatures and less humidity. This period is comfortable for outdoor walks and lake activities.

  • What are the best places to visit in Windermere?

    The historic downtown, scenic lakefront parks, and neighborhood gardens are often recommended for their charm. Art spaces and local markets offer a glimpse into Windermere's creative and community spirit.

  • What are some hiking trails in Windermere?

    Stroll through shaded neighborhood trails and enjoy the boardwalks and paths winding around the local lakes. Nature preserves near Windermere often have well-kept walking routes for gentle hikes.

  • What are some family activities we can do in Windermere?

    Families enjoy picnics at quiet parks, lakeside walks, and renting kayaks or paddleboards. Local markets and community events are also frequently suggested for a relaxed day out together.

  • What are some of the best day trip ideas from Windermere?

    You can explore nearby theme parks, visit tranquil lakes and nature preserves, or experience the local arts and gardens in surrounding towns. Outdoor adventure spots and family attractions are also frequently suggested for memorable outings around Windermere.

  • Are there any pet friendly accommodations available in Windermere?

    Many accommodations in Windermere welcome pets, particularly private homes and rentals near parks or green spaces. Outdoor patios and walking paths make it easy to include your pet in your stay.

  • What are some local tips for visiting Windermere?

    Locals suggest starting mornings with a walk around the lakes or a visit to a neighborhood bakery. Pausing to enjoy the small-town atmosphere and exploring farmers markets can add a relaxed touch to your stay.

  • What is Windermere known for?

    Windermere is known for its tree-lined neighborhoods, chain of tranquil lakes, and small-town atmosphere. The area has a blend of local history, outdoor recreation, and a close-knit community vibe.

  • What are the best hidden gems to explore in Windermere?

    Windermere has tucked-away gardens, small art galleries, and peaceful walking trails that provide a chance to enjoy its quieter side. Locals sometimes point to charming historic sites and unique coffee shops as under-the-radar spots.

  • What are the best foods to try in Windermere?

    Windermere has a range of flavors, with Southern-inspired comfort foods, fresh seafood, and locally made pastries often recommended. Farm-to-table menus and international cuisines reflect the area's diverse community.

  • What should I bring for a trip to Windermere?

    Bring light clothing for warm days, a rain jacket for summer showers, and comfortable shoes for walking. A hat, sunscreen, and reusable water bottle are useful for outdoor outings around the lakes and parks.

  • What is the nightlife in Windermere like?

    Windermere has a calm nightlife scene, with local bistros, wine bars, and coffee shops where gatherings are relaxed and community-oriented. For livelier venues or music, neighboring towns are often frequented.

  • What are the most popular events or festivals in Windermere?

    Windermere has seasonal festivals, art fairs, and community gatherings, often centered around local parks or the historic district. Holiday parades and outdoor markets are popular occasions for neighbors and visitors.

  • Are there family friendly vacation rentals in Windermere?

    Windermere has a variety of family-friendly vacation rentals, including spacious homes, lakefront properties, and residences in quiet neighborhoods. Many are equipped with amenities like kitchens, outdoor areas, and pools for added convenience.

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