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Search results; Over 1,000 homes in Webster

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Top guest favourite
Farm stay in Webster
Welcome happy Campers, have fun!
2 bedrooms, 3 beds, 1 private bathroom
5–10 Oct
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4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Webster
Webster House Your Central Florida Home Base
3 bedrooms, 3 queen beds, 2.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 76 reviews
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Guest favourite
Cabin in Bushnell
Cabin in the Country
2 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 128 reviews
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Top guest favourite
Home in Wildwood
The Villages - Sunshine and pickleball
4 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Place to stay in Brooksville
Epic Outdoor Adventure Await Your Group! Sleep 34
11 bedrooms, 19 beds, 8 bathrooms
18–23 Oct
5.0 out of 5 average rating, 7 reviews
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Superhost
Home in Clermont
2026 Themed 7BR | LED Pool | Windsor Cay
7 bedrooms, 7 beds, 6 bathrooms
14–19 Nov
New place to stay
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Superhost
Home in Clermont
2026 Themed 10 Bedrooms At Windsor Cay
10 bedrooms, 15 beds, 8 bathrooms
3–8 Jan
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Superhost
Home in Kissimmee
NEW 2026 Themed 9BR| Racing Simulator |Solara
9 bedrooms, 13 beds, 6.5 bathrooms
14–19 Dec
4.75 out of 5 average rating, 4 reviews
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Guest favourite
Camper van/Motorhome in Webster
Glamping Camper in the Forest.
1 bedroom, 1 double bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Farm stay in Dade City
Diego’s Cabin-Grounding 18 Acre Wildlife Sanctuary
2 beds, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 78 reviews
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Superhost
Home in Clermont
10 Bd/ 8 Ba/ Windsor Cay (1003 Cr)
10 bedrooms, 15 beds, 8 bathrooms
16–21 Nov
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Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Wildwood
Three Palms Designer Home 3/2 + Golf Car
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
4.98 out of 5 average rating, 40 reviews
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Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1028 Bp)
7 bedrooms, 10 beds, 5 bathrooms
9–14 Nov
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Superhost
Townhouse in Davenport
Spacious 5-BR Villa with Private Pool / Families
5 bedrooms, 8 beds, 4.5 bathrooms
8–13 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
7–12 Oct
5.0 out of 5 average rating, 89 reviews
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Home in Groveland
Nature, Disney & More! Family Home in Groveland
4 bedrooms, 8 beds, 2 bathrooms
9–14 Oct
5.0 out of 5 average rating, 4 reviews
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Superhost
Townhouse in Clermont
5Bd/ 4Ba/ Windsor Cay Resort (16197 Pf)
5 bedrooms, 7 beds, 4.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Tavares
Lake Dora Dream-Waterfront/Pool
4 bedrooms, 5 beds, 4 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 163 reviews