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Search results; Over 1,000 homes in Winter Springs

Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Lake Mary
Casa Alma Vacation Home Steps from LM Event Center
4 bedrooms, 8 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 37 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Sanford
Sunny In Sanford w/Heated Pool
5 bedrooms, 9 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Apartment in Casselberry
Cozy Private Apartment in Casselberry
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Sanford
Spacious 4BR Family Home Near Sanford Airport
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
9–16 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Longwood
The Tiki Palm | Private Resort + Arcade + Pool
4 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 41 reviews
Superhost
Home in Kissimmee
3 Epic Theme Rooms • Sleeps 27 • Pool/Spa • Disney
9 bedrooms, 14 beds, 7.5 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Home in Longwood
The Laurel - Beautiful cottage on private acreage
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Sanford
Modern Farm House, Fenced In Yard. Private Entry!
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 44 reviews
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed, 1 bathroom
11–16 Sept
New place to stay
Superhost
Home in Kissimmee
NEW Lois Ann's Disney Landing 4 miles to entrance!
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
New place to stay
Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 96 reviews
Guest favourite
Guest house in Sanford
The Nook
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 10 reviews