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
Guest suite in Altamonte Springs
4.96 out of 5 average rating, 142 reviewsComfortable Guest Suite-Stylish Altamonte Springs!
Sep 10 – 17
Guesthouse in Sanford
4.95 out of 5 average rating, 227 reviewsPalmetto Pool Retreat
Nov 18 – 25
Home in Altamonte Springs
4.97 out of 5 average rating, 277 reviewsEclectic Home Where Luxury Meets Affordability
Sep 6 – 13
Guest suite in Lake Mary
4.96 out of 5 average rating, 288 reviewsStylish & spa like Getaway - peaceful garden suite
Jul 29 – Aug 5
Bungalow in Winter Park
4.98 out of 5 average rating, 236 reviewsCozy 2/2 Bungalow - Downtown Winterpark/Orlando
Aug 29 – Sep 5
Guest suite in Lake Mary
4.95 out of 5 average rating, 104 reviewsQuiet, Upscale Studio
Aug 27 – Sep 3
Treehouse in Saint Cloud
4.97 out of 5 average rating, 800 reviewsTreeHouse in the Cloud, (Close toTheme Parks
Apr 8 – 15
Guesthouse in Maitland
4.98 out of 5 average rating, 118 reviewsPrivate 1-bd Mid-Century Guesthouse
Jul 13 – 20
Other great vacation rentals in Winter Springs
Home in Casselberry
5.0 out of 5 average rating, 17 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
Oct 10 – 17
Home in Winter Springs
4.96 out of 5 average rating, 26 reviewsJust like home-specious 4 bedroom
Sep 6 – 13
Guesthouse in Lake Mary
4.96 out of 5 average rating, 24 reviewsRelaxing Cozy Cottage w/ Queen Bed & Private Lanai
May 25 – Jun 1
Guesthouse in Lake Mary
4.97 out of 5 average rating, 67 reviewsCozy Cottage in the heart of Lake Mary
Jul 18 – 25
Guesthouse in Longwood
5.0 out of 5 average rating, 67 reviews"Winnie's Place" A Peaceful Guesthouse with Pool.
Apr 6 – 13
Guesthouse in Oviedo
4.89 out of 5 average rating, 19 reviewsCozy Knight Stay
Nov 24 – Dec 1
Apartment in Orlando
5.0 out of 5 average rating, 72 reviewsParent's Retreat!
Jul 21 – 28
Cottage in Altamonte Springs
4.99 out of 5 average rating, 99 reviews"One of a Kind" Private Lakefront Getaway
Sep 19 – 26
Quick stats about vacation rentals in Winter Springs
Total rentals
80 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
2.9K reviews
Nightly prices starting at
$10 before taxes and fees
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 20 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 50 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 50 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 50 homes with air conditioning, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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