Holiday rentals in Windermere
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Windermere
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest house in Orlando
4.94 out of 5 average rating, 207 reviewsModern Guest Studio (Private) Pool / Spa available
Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.
31 Dec – 7 Jan
Home in Winter Garden
4.92 out of 5 average rating, 164 reviewsCozy 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.
1–8 May
Cottage in Winter Garden
4.99 out of 5 average rating, 102 reviewsCome Stay In The Heart Of Winter Garden
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.
20–27 Aug
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windermere holiday rentals
Other great holiday rentals in Windermere
Home in Orlando
4.94 out of 5 average rating, 227 reviewsNew studio in a newly renovated House
21–28 Oct
Guest house in Orlando
4.82 out of 5 average rating, 435 reviewsSpacious getaway close to Universal and Outlets!
22–29 Nov
Home in Apopka
4.96 out of 5 average rating, 184 reviewsFarm feel in the city
30 Jan – 6 Feb
Flat in Windermere
5.0 out of 5 average rating, 17 reviews1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym
16–23 Aug
Flat in Windermere
4.83 out of 5 average rating, 52 reviewsPrivate Garage Apt., 5 Miles from Disney World
7–14 Oct
Flat in Windermere
5.0 out of 5 average rating, 17 reviews2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi
25 May – 1 Jun
Apartment in Windermere
5.0 out of 5 average rating, 11 reviewsLuXury Apt with Lake View, Cable & fast WiFi
31 Aug – 7 Sept
Home in Winter Garden
4.88 out of 5 average rating, 16 reviewsPet Friendly Winter Garden Get-Away near Orlando
22–29 Sept
Guest house in Winter Garden
4.94 out of 5 average rating, 47 reviewsBlue Heron Bungalow
11–18 Jul
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
4–11 Jul
Flat in Ocoee
4.96 out of 5 average rating, 47 reviewsCompletely Private and Cozy Studio
8–15 Aug
Cottage in Winter Garden
4.89 out of 5 average rating, 84 reviews3 br/2 ba Downtown Winter Garden Cottage w\fence
22–27 Mar
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- West Palm Beach Holiday rentals
- Naples Holiday rentals
- Boca Raton Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Key West Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom