House holiday rentals in Winter Springs
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Top-rated house rentals in Winter Springs
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Springs house rentals
House rentals with a pool
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
24–31 Aug
Home in Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
14–21 May
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
9–16 Aug
Home in Deltona
4.96 out of 5 average rating, 149 reviewsSt. John’s Luxury Pool Lake House
8–15 Jun
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
25 Mar – 1 Apr
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
12–19 Dec
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
24–31 Mar
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
24–31 Jan
Weekly house rentals
Home in Sanford
4.93 out of 5 average rating, 164 reviews“The Shed" in Historic Downtown Sanford
14–21 Oct
Home in Altamonte Springs
4.83 out of 5 average rating, 161 reviewsGuest House near attractions
21–28 Aug
Home in Sanford
4.87 out of 5 average rating, 101 reviewsBeautiful & sweet house ready for your vacation!!!
24–31 Jul
Home in Altamonte Springs
4.83 out of 5 average rating, 107 reviewsElegant, Spacious Three Bedroom Residential House.
12–19 Jul
Home in Winter Garden
4.92 out of 5 average rating, 166 reviewsCozy Winter Garden Home 20 MINUTES FROM DISNEY
20–27 Jul
Home in Orlando
4.91 out of 5 average rating, 179 reviewsCozy Milk District Home | Downtown | Free Parking
17–24 Aug
Home in Orlando
4.86 out of 5 average rating, 227 reviewsCozy Cottage at University
22–29 Jun
Home in Leesburg
4.97 out of 5 average rating, 220 reviewsPeace and Quiet
26 Jun – 3 Jul
Private house rentals
Home in Altamonte Springs
5.0 out of 5 average rating, 29 reviewsOrlando's Cozy & Private Studio Altamonte Springs
19–26 Aug
Home in Winter Park
5.0 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
30 May – 6 Jun
Home in Longwood
4.9 out of 5 average rating, 58 reviewsPeaceful retreat family friendly home with parking
9–16 Sep
Home in Winter Springs
4.94 out of 5 average rating, 83 reviewsModern Lakefront House (Family Friendly)
14–21 Apr
Home in Longwood
5.0 out of 5 average rating, 33 reviewsOne Love Retreat and Guest House
11–18 Mar
Home in Sanford
4.95 out of 5 average rating, 81 reviewsThe Golf-view House (Entire House, King bedroom)
27 Mar – 3 Apr
Home in Oviedo
4.97 out of 5 average rating, 68 reviewsCasa Nero 3/2 Eclectic vintage farmhouse near UCF
9–16 May
Home in Sanford
4.98 out of 5 average rating, 86 reviewsThe Cypress House
27 Sep – 4 Oct
Quick stats about house rentals in Winter Springs
Total rentals
50 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
$17 NZD before taxes and fees
Destinations to explore
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