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Search results; Over 1,000 homes in Winter Springs

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Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Lake Mary
Casa Alma Vacation Home Steps from LM Event Center
4 bedrooms, 8 beds
4–9 Oct
4.97 out of 5 average rating, 38 reviews
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Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds
11–16 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Sanford
Spacious 4BR Family Home Near Sanford Airport
4 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds
3–8 Oct
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Longwood
The Tiki Palm | Private Resort + Arcade + Pool
4 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
22–29 Sept
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed
21–26 Sept
5.0 out of 5 average rating, 6 reviews
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Home in Altamonte Springs
The Altamonte Playground: Large Renovated Home
4 bedrooms, 5 beds
7–12 Dec
New place to stay
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Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Superhost
Home in Sanford
Modern home near Sanford's Historic District
4 bedrooms, 5 beds
23–30 Sept
5.0 out of 5 average rating, 3 reviews
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Flat in Orlando
Private 2-Queen Apt Near MCO with Patio
1 bedroom, 3 beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Guest house in Sanford
The Nook
1 queen bed
9–14 Oct
5.0 out of 5 average rating, 12 reviews
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Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds
9–14 Nov
New place to stay
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Home in Lake Mary
Southern Homestead
3 bedrooms, 3 beds
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 9 reviews
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Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 47 reviews