Winter Springs vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winter Springs
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Springs vacation rentals
Other great vacation rentals in Winter Springs
Home in Davenport
4.78 out of 5 average rating, 23 reviewsSolterra discount slps 18/7 bdm/GR/pool/spa5485
This was a wonderful home for our entire family! (Our Grandkids all enjoyed being under one roof) It was spacious, clean & beautiful. Perfect for families with children. Loved the layout (especially the large loft with extra living space) , pool & play area in garage. The kitchen was fully equipped! The house also had a high chair, pack n play & stroller which was so helpful. We enjoyed the clubhouse in the neighbor as well! Pickle ball courts & crafts for kids at their pool every day. Susan was an exceptional host and an excellent communicator. So kind! Would highly recommend!
Home in Davenport
4.84 out of 5 average rating, 19 reviewsLuxe Retreat - Beautiful Modern 7 Bedrooms Home
Absolutely stunning house.
Home in Davenport
5 out of 5 average rating, 4 reviewsNew! Windsor Island Resort with pool by Disney 03
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.
Townhouse in Kissimmee
4.93 out of 5 average rating, 183 reviewsBeautiful family home near all attractions.
Thanks for everything! It was nice and comfortable. Perfect spot for Disneyland & Co.!
Home in Kissimmee
4.81 out of 5 average rating, 21 reviewsVacation Home with Pool & Spa near Disney
It was very peaceful and a nice house! Thank you
Home in Kissimmee
5 out of 5 average rating, 7 reviewsAmazing townhouse in Champions Gate
We enjoyed our first ever Airbnb stay in the Florida area. The amenities were amazing for the local resort, the pool located at the property was positioned perfectly for me to see my children playing on the patio/ pool area while in the kitchen. We loved the outdoor seating and bbq grill. Gabe & Gabrielle were responsive, they always made sure to respond timley with any questions we had. We also loved the QR code in the entry way, you scan it and it displays all the amenities from resort, closing times, and different themes or specials at the local grill. We had an amazing first trip & thankful for the opportunity to stay at this property! Active duty family & will be back!
Home in Kissimmee
4.81 out of 5 average rating, 32 reviews2611-VP Beautiful 4 Bd Home, Lake View & Pool
We loved our stay! We give this house 5 stars and would recommend this place to others. The home was clean, had comfortable beds, fully stocked kitchen, and plenty of room for everyone! We felt right at home! The pool was clean and a good size. The location is great-close to plenty of places to shop, eat, and check out. The neighborhood was quiet and safe. My teenage boys also enjoyed the workout facilities at the club house. This home was perfect for our family! Thank you!!!
Home in Orlando
4.93 out of 5 average rating, 27 reviewsRelaxing four bedroom getaway built 4 long stays
Edwin’s place was in a quiet area with decent food options nearby (Walmart less than 10 minutes away). We stayed here for EDC Orlando and this spot was only about a 20 minute Uber away from the stadium. Edwin was very responsive and accommodating!
Quick stats about vacation rentals in Winter Springs
Total rentals
80 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Winter Springs?
Yes! Work meets play with ease at over 30 vacation rentals in Winter Springs featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Springs?
Four-legged friends are welcome in Winter Springs. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Winter Springs vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Winter Springs, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Winter Springs?
Experience the best of Winter Springs with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winter Springs have wireless internet?
Absolutely! We offer over 40 house rentals with wireless internet in Winter Springs. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winter Springs?
Winter Springs has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Springs have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Winter Springs. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winter Springs?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wireless internet, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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