Vacation rentals in Winter Springs
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winter Springs
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
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 favourite
Guesthouse in Sanford
4.94 out of 5 average rating, 192 reviewsPrivate Courtyard Cottage on Canal
Jul. 23 – 30
$143 CAD per night
Guest favourite
Home in Maitland
4.97 out of 5 average rating, 118 reviewsThe Butterfly Bungalow near Park Ave
Oct. 23 – 30
$230 CAD per night
Guest favourite
Bungalow in Winter Park
4.98 out of 5 average rating, 235 reviewsCozy 2/2 Bungalow - Downtown Winterpark/Orlando
Jun. 10 – 17
$221 CAD per night
Guest favourite
Treehouse in Saint Cloud
4.97 out of 5 average rating, 793 reviewsTreeHouse in the Cloud, (Close toTheme Parks
Apr. 14 – 21
$263 CAD per night
Guest favourite
Guest suite in Winter Springs
4.97 out of 5 average rating, 66 reviewsModern Guest Studio 15 mins from SFB Airport
Sep. 3 – 10
$127 CAD per night
Guest favourite
Home in Winter Springs
4.96 out of 5 average rating, 25 reviewsJust like home-specious 4 bedroom
Oct. 13 – 20
$363 CAD per night
Guest favourite
Guesthouse in Lake Mary
4.97 out of 5 average rating, 65 reviewsCozy Cottage in the heart of Lake Mary
Sep. 1 – 8
$133 CAD per night
Guest favourite
Guesthouse in Oviedo
5.0 out of 5 average rating, 17 reviewsCozy Knight Stay
Feb. 7 – 14
$191 CAD per night
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
$14 CAD before taxes and fees
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