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
Guesthouse in Sanford
4.94 out of 5 average rating, 190 reviewsPrivate Courtyard Cottage on Canal
May 31 – Jun 7
Home in Winter Park
4.9 out of 5 average rating, 129 reviewsGuest Suite in Winter Park/Orlando
Jul 6 – 13
Apartment in Maitland
4.82 out of 5 average rating, 251 reviewsAt Mine | Elegant Double Suite in North Orlando
Sep 28 – Oct 5
Home in Maitland
4.96 out of 5 average rating, 114 reviewsThe Butterfly Bungalow near Park Ave
Sep 12 – 19
Guesthouse in Sanford
4.95 out of 5 average rating, 225 reviewsPalmetto Pool Retreat
Feb 20 – 27
Bungalow in Winter Park
4.98 out of 5 average rating, 231 reviewsCozy 2/2 Bungalow - Downtown Winterpark/Orlando
Jun 13 – 20
Guest suite in Lake Mary
4.95 out of 5 average rating, 103 reviewsQuiet, Upscale Studio
Oct 13 – 20
Home in Altamonte Springs
4.97 out of 5 average rating, 273 reviewsEclectic Home Where Luxury Meets Affordability
Jul 21 – 28
Other great vacation rentals in Winter Springs
Guesthouse in Longwood
5.0 out of 5 average rating, 65 reviews"Winnie's Place" A Peaceful Guesthouse with Pool.
Nov 6 – 13
Guesthouse in Lake Mary
4.98 out of 5 average rating, 63 reviewsCozy Cottage in the heart of Lake Mary
Aug 26 – Sep 2
Guest suite in Winter Park
4.94 out of 5 average rating, 82 reviewsRomantic Villa at Winter Park 1Bed 1Bath
Dec 5 – 12
Home in Casselberry
5.0 out of 5 average rating, 42 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
Mar 30 – Apr 6
Home in Longwood
4.9 out of 5 average rating, 58 reviewsPeaceful retreat family friendly home with parking
Dec 12 – 19
Apartment in Orlando
5.0 out of 5 average rating, 67 reviewsParent's Retreat!
Aug 2 – 9
Guesthouse in Longwood
4.89 out of 5 average rating, 28 reviewsCozy and Modern Studio suite in Longwood
May 1 – 8
Guesthouse in Oviedo
5.0 out of 5 average rating, 14 reviewsCozy Knight Stay
Feb 17 – 24
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
ﺩ.ﺇ37 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.
Destinations to explore
- Orlando Vacation rentals
- Kissimmee Vacation rentals
- Tampa Vacation rentals
- Anna Maria Island Vacation rentals
- Sarasota Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Naples Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Beach Vacation rentals
- Miami Vacation rentals
- Key West Vacation 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