House vacation rentals in Winter Springs
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Springs
Guests agree: these houses 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 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.
Aug 24 – 31
Home in Deltona
4.96 out of 5 average rating, 149 reviewsSt. John’s Luxury Pool Lake House
Jun 8 – 15
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Dec 20 – 27
Home in Altamonte Springs
4.82 out of 5 average rating, 110 reviewsQuiet Place, convenient to everything!
Aug 23 – 30
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
Mar 24 – 31
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Jul 22 – 29
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
Aug 21 – 28
Home in Deltona
4.94 out of 5 average rating, 110 reviewsExecutive Lake House w/Solar Heated Saltwater Pool
Jul 15 – 22
Weekly house rentals
Home in Sanford
4.87 out of 5 average rating, 101 reviewsBeautiful & sweet house ready for your vacation!!!
Nov 21 – 28
Home in Altamonte Springs
4.83 out of 5 average rating, 161 reviewsGuest House near attractions
Aug 22 – 29
Home in Sanford
4.9 out of 5 average rating, 142 reviewsThe Sanford House
Jul 12 – 19
Home in Winter Garden
4.92 out of 5 average rating, 166 reviewsCozy Winter Garden Home 20 MINUTES FROM DISNEY
Jul 20 – 27
Home in Orlando
4.91 out of 5 average rating, 179 reviewsCozy Milk District Home | Downtown | Free Parking
Aug 17 – 24
Home in Orlando
4.86 out of 5 average rating, 227 reviewsCozy Cottage at University
Jun 8 – 15
Home in Altamonte Springs
4.83 out of 5 average rating, 107 reviewsElegant, Spacious Three Bedroom Residential House.
Mar 2 – 9
Home in Orlando
4.81 out of 5 average rating, 150 reviewsKing suite , Modern house perfect for vacation
Dec 6 – 13
Private house rentals
Home in Longwood
4.9 out of 5 average rating, 58 reviewsPeaceful retreat family friendly home with parking
Aug 29 – Sep 5
Home in Longwood
5.0 out of 5 average rating, 33 reviewsOne Love Retreat and Guest House
Oct 2 – 9
Home in Winter Springs
4.94 out of 5 average rating, 83 reviewsModern Lakefront House (Family Friendly)
Jan 20 – 27
Home in Winter Park
5.0 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
Sep 1 – 8
Home in Sanford
4.95 out of 5 average rating, 81 reviewsThe Golf-view House (Entire House, King bedroom)
Jan 6 – 13
Home in Oviedo
4.97 out of 5 average rating, 68 reviewsCasa Nero 3/2 Eclectic vintage farmhouse near UCF
May 9 – 16
Home in Sanford
4.98 out of 5 average rating, 86 reviewsThe Cypress House
Mar 29 – Apr 5
Home in Orlando
5.0 out of 5 average rating, 31 reviewsLuxurious and modern cottage near UCF
Oct 14 – 21
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
€ 9 before taxes and fees
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