Vacation rentals in Winter Springs

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Top-rated vacation rentals in Winter Springs

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Townhouse in Winter Park
Beautiful Downtown Winter Park
WP requires rentals to be listed as 28 days. For alternate rentals please contact me with dates requested. A 1 bedroom New England style townhouse. Enjoy brick streets, old oaks and lake access all within a 5 minute walk to downtown Winter Park, home of nationally known art festivals and museums, Saturday farmers market, Rollins College and many fine dining establishments. Pick herbs from our garden to use in cooking. Lounge on your private deck to the relaxing waterfall sounds of our koi pond.
Jun. 15 – 22
$212 CAD per night
4.98 out of 5 average rating, 193 reviews
Guest favourite
Bungalow in Maitland
Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.
Aug. 22 – 29
$143 CAD per night
4.86 out of 5 average rating, 484 reviews
Guest favourite
Guest suite in Altamonte Springs
St Augustine suite
Luxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting
Jun. 8 – 15
$143 CAD per night
4.95 out of 5 average rating, 310 reviews

Popular amenities for Winter Springs vacation rentals

Stay near Winter Springs's top sights

Oviedo Mall16 locals recommend
Townhouse Restaurant15 locals recommend
Regal Oviedo Mall10 locals recommend
Spring Hammock Preserve6 locals recommend
Publix Super Market at Winter Springs Town Center3 locals recommend
Target6 locals recommend

Other great vacation rentals in Winter Springs

Guest favourite
Guest suite in Altamonte Springs
Comfortable Guest Suite-Stylish Altamonte Springs!
Sep. 14 – 21
$187 CAD per night
4.96 out of 5 average rating, 137 reviews
Guest favourite
Guest suite in Altamonte Springs
The Bungalow
Jun. 12 – 19
$171 CAD per night
4.92 out of 5 average rating, 314 reviews
Guest favourite
Home in Altamonte Springs
Eclectic Home Where Luxury Meets Affordability
Aug. 24 – 31
$326 CAD per night
4.97 out of 5 average rating, 274 reviews
Guest favourite
Home in Winter Park
Guest Suite in Winter Park/Orlando
Apr. 28 – May 5
$120 CAD per night
4.9 out of 5 average rating, 120 reviews
Guest favourite
Guest suite in Lake Mary
Stylish & spa like Getaway - peaceful garden suite
Apr. 12 – 19
$237 CAD per night
4.96 out of 5 average rating, 280 reviews
Guest favourite
Guest suite in Winter Springs
Modern Guest Studio 15 mins from SFB Airport
Oct. 11 – 18
$136 CAD per night
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in Winter Springs
Just like home-specious 4 bedroom
May 2 – 9
$359 CAD per night
4.96 out of 5 average rating, 24 reviews
Guest favourite
Guesthouse in Longwood
"Winnie's Place" A Peaceful Guesthouse with Pool.
Oct. 5 – 12
$206 CAD per night
5.0 out of 5 average rating, 62 reviews
Superhost
Home in Winter Springs
Pure Vida - Your home away from home!
Jun. 21 – 28
$300 CAD per night
4.86 out of 5 average rating, 7 reviews
Superhost
Home in Winter Park
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May 10 – 17
$228 CAD per night
4.9 out of 5 average rating, 39 reviews
Guest favourite
Home in Winter Springs
Modern Lakefront House (Family Friendly)
Jan. 23 – 30
$390 CAD per night
4.94 out of 5 average rating, 82 reviews
Guest favourite
Guesthouse in Lake Mary
Cozy Cottage in the heart of Lake Mary
Aug. 11 – 18
$137 CAD per night
4.98 out of 5 average rating, 56 reviews

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

2.8K reviews

Nightly prices starting at

$14 CAD before taxes and fees

Destinations to explore