Compare Vacation Rentals & Airbnb in Windermere, FL

21 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Windermere, FL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

21 Rentals and Airbnb in Windermere, FL

Best family friendly Windermere, FL vacation rentals

Among the 21 accommodations in Windermere, FL, here are the 4 best family friendly rentals

Walk To Dtwn: Winter Garden Home W/ Patio - Windermere, FL
9.8 138 reviews

Walk To Dtwn: Winter Garden Home W/ Patio

house, Winter Garden
This spacious Winter Garden home is located just a short walk from the town centre, 12 miles from Disney's Magic Kingdom and 13 miles from Camping World Stadium, making it ideal for exploring the area. The property has received excellent ratings for location, cleanliness, and overall experience.
This two-bedroom home spans 93 square metres and can comfortably accommodate up to four guests. The property features a well-equipped kitchen, a relaxing garden with a spa, and free Wi-Fi throughout.
Epicentric Condo, Universal, Disney - Windermere, FL
No reviews

Epicentric Condo, Universal, Disney

apartment, Orlando
This two-bedroom, one-bathroom flat is situated in Orlando's International Drive District, placing it within 2 kilometres of The Orlando Eye and Universal CityWalk, and a short drive from Orlando International Premium Outlets and Florida Mall.
This 46 square meter apartment accommodates up to four guests and features a fully equipped kitchen, air conditioning, a swimming pool, and parking, with easy access to the Kia Centre and ESPN Wide World of Sports Complex.
Universal's Aventura Hotel - Windermere, FL
8.9 15195 reviews

Universal's Aventura Hotel

resort, Orlando
Universal's Cabana Bay Beach Resort is located right next to Universal's Volcano Bay water theme park and just a mile from Universal Studios Florida, Universal's Islands of Adventure, and Universal CityWalk, making it ideal for exploring all that Orlando has to offer. The resort enjoys very good user ratings for cleanliness and an excellent location rating.
The resort offers a range of accommodation options, from standard rooms to spacious family suites with kitchenettes. Guests can enjoy two swimming pools, a lazy river, a beach, a water slide, a fitness centre, a bowling alley, a games room, and a variety of restaurants and bars.
Rose's Lakeview - Windermere, FL
9.0 22 reviews

Rose's Lakeview

apartment, Pine Hills
This three-bedroom, two-bathroom holiday home in Pine Hills, Florida, is situated 15.8km from downtown Orlando and 32km from Walt Disney World.
Sleeping six guests, the property boasts a fully equipped kitchen including fridge, microwave, and dishwasher; air conditioning; parking; internet access; and tranquil lake views from the master bedroom, kitchen, and dining areas, along with a spacious backyard.

Best Windermere, FL vacation rentals with parking

Home Away From Home! Minutes To Universal & Disney - Windermere, FL
9.1 47 reviews

Home Away From Home! Minutes To Universal & Disney

house, Doctor Phillips
This Doctor Phillips two-bedroom suite offers a private entrance and is located minutes' drive (a few kilometres) from Universal Orlando Resort, SeaWorld Orlando, and Walt Disney World Resort.
The self-contained property sleeps six guests, features a king-size bed, a queen-size bed, a sofa bed, a full bathroom, laundry facilities, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher; complimentary Wi-Fi and cable TV are also provided.
Beautiful Lakefront Villa - Windermere, FL
9.2 340 reviews

Beautiful Lakefront Villa

apartment, Doctor Phillips
This Doctor Phillips lakefront villa is situated 1.1 kilometres from Dr P Phillips Hospital, offering serene views and convenient access to the Orange County Convention Centre and Aquatica, both within 4.8 kilometres.
The self-catering property sleeps four guests in one bedroom and one bathroom, boasting a private balcony, swimming pool, spa, and free Wi-Fi, plus proximity to Orlando Vineland Premium Outlets (4.5km).
Sweet Dreams Studio - Windermere, FL
9.8 45 reviews

Sweet Dreams Studio

house, Orlovista
This Orlovista studio apartment offers excellent location near Universal Studios, Disney World, SeaWorld, and Aquatica, with convenient access to local amenities including pharmacies, supermarkets and restaurants.
The self-catering apartment sleeps two guests and features a fridge, microwave, air conditioning, a garden, parking, and an independent entrance; enjoy exploring Orlovista and its surrounding attractions from this comfortable base.
Winter Garden 2 Bedrooms/2 Bath Home (Downtown) - Windermere, FL
9.6 35 reviews

Winter Garden 2 Bedrooms/2 Bath Home (Downtown)

apartment, Winter Garden
This fully renovated two-bedroom, two-bathroom house in Winter Garden's downtown area is a 48km drive from Walt Disney World Resort and Orlando International Airport, and within walking distance of Lake Jennie Jewel.
The 4-person property boasts a fully equipped kitchen, air conditioning, parking, and internet access, offering easy access to shops, restaurants and Winter Garden's historic district.

Frequently Asked Questions about vacation rentals in Windermere, FL

  • What are some interesting places to visit in or near Windermere, FL?

    Windermere is a great base for exploring Central Florida. You can visit the iconic Walt Disney World Resort, just a short drive away. For something a little different, head to the charming town of Winter Garden, known for its historic downtown and farmers' market. If you're looking for a bit of nature, the Wekiwa Springs State Park offers beautiful hiking trails and swimming in the clear springs.
  • What are the best Airbnb and vacation rentals in Windermere, FL?

    Spacious Getaway Close To Universal And Outlets, Mid-century Modern Villa W/ Pool Near Universal and Paradise Nook Near Orlando's Theme Parks are the most popular Airbnb and vacation rentals in Windermere, FL among travelers.

  • Which walking or cycling routes are the best in Windermere, FL?

    The West Orange Trail is a popular paved path that runs through Windermere, perfect for walking, running, or cycling. It's a lovely way to enjoy the scenery and get some exercise. For a shorter walk, try the scenic loop around Lake Butler, offering beautiful views of the water.
  • What are the most popular Airbnbs in Windermere, FL?

  • What sports or outdoor activites can visitors enjoy in and around Windermere, FL?

    Windermere is a great place for water sports. You can go boating, fishing, or kayaking on Lake Butler. There are also several golf courses in the area, including the exclusive Isleworth Golf & Country Club. For something a little more adventurous, try ziplining at Gatorland, just a short drive away.
  • What are the best vacation rentals with a pool in Windermere, FL?

  • What other towns or cities can be easily accessed from Windermere, FL?

    Windermere is conveniently located near several other towns and cities. You can easily reach Orlando, home to many attractions, in about 20 minutes. Other nearby towns include Winter Garden, Ocoee, and Clermont, each offering unique experiences.
  • What are the best rentals for families and kids in Windermere, FL?

  • What amenities are commonly available in vacation rentals in Windermere, FL?

    Vacation rentals in Windermere usually offer a range of amenities, including private pools, hot tubs, and fully equipped kitchens. Many also have laundry facilities, Wi-Fi, and outdoor living spaces with patios or balconies. Some even have game rooms or home theatres.
  • What are the best rentals or Airbnbs with a jacuzzi in Windermere, FL?

  • What time of year is best to rent a vacation rental Windermere, FL?

    The best time to visit Windermere depends on your preferences. The weather is warm and sunny year-round, but the peak season is during the winter months (November to April) when it's less humid. If you prefer cooler weather, the spring and autumn months are ideal.
  • What are the local dishes in Windermere, FL region?

    Windermere is known for its diverse culinary scene, influenced by its location in Central Florida. You can find everything from classic American dishes to fresh seafood and international cuisine. Some local favourites include Florida stone crab, fresh grouper, and Key lime pie. Don't forget to try the local craft beers and wines.

Popular destinations

Best Windermere, FL vacation rentals with a balcony

Cozy Lakeview Getaway / Near Universal Studios - Windermere, FL
8.2 18 reviews

Cozy Lakeview Getaway / Near Universal Studios

studio, Orlando
This Orlando condo is situated near Pirate's Dinner Adventure and CoCo Key Water Resort, within a short walk, and less than 2km from Universal Orlando Resort and ICON Park.
This two-bedroom apartment, boasting 54 square metres of floor space, features a fully equipped kitchen, two bathrooms, a private balcony, and accommodates up to six guests, with access to an on-site fitness centre and hot tub.
Coco Key Hotel & Water Park Resort - Windermere, FL
8.0 8448 reviews

Coco Key Hotel & Water Park Resort

resort, Orlando
The Coco Key Hotel & Water Park Resort is located near Universal Orlando Resort, just 4.8 kilometres from the theme park and 7.6 kilometres from SeaWorld Orlando. The hotel offers a range of amenities including a large water park with slides, a jungle gym area, and a dedicated children's pool, as well as a restaurant, bar, convenience store, and arcade.
Js Luxury Vacation - Windermere, FL
9.0 1 review

Js Luxury Vacation

apartment, Orlando
This Orlando flat offers scenic river and potential lake views, located 1.9 kilometres from The Wheel At Icon Park and 2.4 kilometres from Universal Studios' Islands of Adventure, with Orlando International Airport 14.9 kilometres away.
This two-bedroom apartment includes air conditioning, complimentary WiFi, a fully equipped kitchen with a dishwasher, oven, and microwave, as well as a balcony, patio, garden, bar, and hot tub, with complimentary private parking provided.
16 Mi To Disney: Cottage W/ Deck In Winter Garden - Windermere, FL
9.7 78 reviews

16 Mi To Disney: Cottage W/ Deck In Winter Garden

house, Winter Garden
This modern cottage is located in Winter Garden, Florida, just 26 kilometres from Walt Disney World and close to other attractions like Camping World Stadium, Amway Center, and Church Street Station. The cottage has received excellent ratings for location, cleanliness, and overall experience.
The cottage has one bedroom and one bathroom, covering 49 square metres and accommodating up to four guests. Amenities include a fully equipped kitchen, a private patio, air conditioning, free Wi-Fi, and a washer and dryer, making it a comfortable and convenient choice for travellers.

Best pet friendly Windermere, FL vacation rentals

Among the 21 accommodations in Windermere, FL, here are the 4 best pet friendly rentals

Luxury 1br With Resort Amenities 6min To Epic&uni - Windermere, FL
10 13 reviews

Luxury 1br With Resort Amenities 6min To Epic&uni

apartment, Orlando
This modern 1-bedroom flat in Orlando, Florida, is conveniently located just 7 minutes from Universal Orlando Resort, 4 minutes from ICON Park, and 20-25 minutes from Walt Disney World Resort.
This pet-friendly accommodation offers a fully equipped kitchen, air conditioning, a swimming pool, a fitness centre, and free covered garage parking, comfortably accommodating up to four guests.
Cozy 1-bedroom Condo In Charming Orlando With Ac And Fitness Room Near Universal - Windermere, FL
10 3 reviews

Cozy 1-bedroom Condo In Charming Orlando With Ac And Fitness Room Near Universal

apartment, Doctor Phillips
This one-bedroom flat in Orlando, Doctor Phillips, offers convenient access to attractions such as Disney Springs™ (4.8 km) and Universal’s Volcano Bay (1.6 km), with the Orange County Convention Centre also within walking distance.
This serviced apartment accommodates up to four guests with a king bed and a queen sofa bed, featuring a kitchenette with essential appliances, air conditioning, and access to a communal swimming pool and fitness room.
1 Full Bed  Micfridge - Windermere, FL
No reviews

1 Full Bed Micfridge

apartment, Orlando
This studio flat is situated on International Drive, placing guests 1.9 kilometres from Universal Studios Florida and 14.5 kilometres from Walt Disney World Resort.
This pet-friendly accommodation offers a swimming pool, complimentary WiFi, and free coffee, with a floor area of 19 square metres suitable for up to two guests.
Cozy Studio Apt #5 By Bike Trail & Historic Downtown Winter Garden - Windermere, FL
No reviews

Cozy Studio Apt #5 By Bike Trail & Historic Downtown Winter Garden

studio, Winter Garden
This studio apartment in Winter Garden is located within walking distance of the West Orange Trail and the Winter Garden Historic Museum, offering convenient access to local attractions.
This accommodation for two guests provides a kitchenette with a fridge and microwave, air conditioning, complimentary Wi-Fi, and on-site parking.
©2026 cozycozy.com