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Search results; Over 1,000 homes in Longwood

Top guest favourite
Guest house in Longwood
"Winnie's Place" A Peaceful Guesthouse with Pool.
1 bedroom, 3 beds, 1 private bathroom
29 Sept – 4 Oct
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4.98 out of 5 average rating, 143 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
15–22 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
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Longwood
The Laurel - Beautiful cottage on private acreage
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 55 reviews
Home in Lake Mary
Southern Homestead
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Home in Longwood
New Home in Historic Longwood
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Mar
4.83 out of 5 average rating, 6 reviews
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 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
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Sanford
Spacious 4BR Family Home Near Sanford Airport
4 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
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, 24 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 65 reviews
Hotel in Lake Mary
*30 miles From Orlando + Free Breakfast & Pool
3 beds, 1 bathroom
13–18 Sept
Room in Apopka
Apopka HideAway Rm 2
1 bed, 1 bathroom
15–20 Sept
New place to stay
Guest favourite
Guest house in Sanford
The Nook
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Kissimmee
Private Pool • No Resort Fee | 10 Min to Disney
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Home in Sanford
Walk Everywhere! Historic Sanford Home w/ Patio
2 bedrooms, 2 beds, 1.5 bathrooms
11–16 Oct
Guest favourite
Home in Sanford
Sunny In Sanford w/Heated Pool
5 bedrooms, 9 beds, 2 bathrooms
14–19 Sept
4.94 out of 5 average rating, 16 reviews