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 house rentals in Winter Springs
House rentals with a pool
Home in Deltona
4.96 out of 5 average rating, 150 reviewsSt. John’s Luxury Pool Lake House
15–22 Jan
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
31 Oct – 7 Nov
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
15–22 Sep
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
23–30 Aug
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
10–17 Jun
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
4–11 Apr
Home in Deltona
4.94 out of 5 average rating, 110 reviewsExecutive Lake House w/Solar Heated Saltwater Pool
15–22 Jul
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
23 Feb – 2 Mar
Weekly house rentals
Home in Sanford
4.97 out of 5 average rating, 152 reviewsFamous Tiny Houseboat Historic Downtown Sanford FL
21–28 Sep
Home in Altamonte Springs
4.83 out of 5 average rating, 162 reviewsGuest House near attractions
20–27 Jul
Home in Sanford
4.9 out of 5 average rating, 143 reviewsThe Sanford House
12–19 Jul
Home in Altamonte Springs
4.83 out of 5 average rating, 108 reviewsElegant, Spacious Three Bedroom Residential House.
2–9 Mar
Home in Orlando
4.86 out of 5 average rating, 227 reviewsCozy Cottage at University
8–15 Jun
Home in Orlando
4.81 out of 5 average rating, 151 reviewsKing suite , Modern house perfect for vacation
23–30 Dec
Home in Winter Springs
4.96 out of 5 average rating, 25 reviewsJust like home-specious 4 bedroom
28 Aug – 4 Sep
Home in Altamonte Springs
4.92 out of 5 average rating, 52 reviewsRenovated Peaceful Luxury Walk to Mall Park Publix
14–21 Dec
Private house rentals
Home in Winter Springs
4.94 out of 5 average rating, 83 reviewsModern Lakefront House (Family Friendly)
20–27 Jan
Home in Winter Park
5.0 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
22–29 Sep
Home in Sanford
4.95 out of 5 average rating, 81 reviewsThe Golf-view House (Entire House, King bedroom)
16–23 Mar
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
13–20 Jan
Home in Orlando
5.0 out of 5 average rating, 31 reviewsLuxurious and modern cottage near UCF
29 Sep – 6 Oct
Home in Sanford
4.94 out of 5 average rating, 35 reviewsBright & Airy in DowntownSanford
25 Dec – 1 Jan
Home in Oviedo
4.86 out of 5 average rating, 14 reviewsComplete Modern House
8–15 Aug
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
1.5T reviews
Nightly prices starting at
₹834 before taxes and fees
Destinations to explore
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