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Search results; Over 1,000 homes in Longwood

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Guest favourite
Home in Longwood
Recharge @ Timberland Lodge: Pool Hottub Sauna
4 bedrooms, 6 beds, 2.5 private bathrooms
1–6 Oct
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4.88 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
1–8 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Longwood
The Tiki Palm | Private Resort + Arcade + Pool
4 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 24 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, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 38 reviews
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Home in Lake Mary
Southern Homestead
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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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
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Top guest favourite
Home in Longwood
The Laurel - Beautiful cottage on private acreage
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 55 reviews
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Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
5.0 out of 5 average rating, 3 reviews
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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, 25 reviews
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Home in Altamonte Springs
The Altamonte Playground: Large Renovated Home
4 bedrooms, 5 beds, 2 bathrooms
7–12 Dec
New place to stay
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Home in Orlando
The Escape Village | 8 PPL | Pool | Fire Pit | BBQ
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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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
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Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Guest house in Sanford
The Nook
1 queen bed, 1 bathroom
6–11 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 23 reviews
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Superhost
Home in Kissimmee
9BR house sleeps 24 with spa and pool
9 bedrooms, 14 beds, 5 bathrooms
29 Oct – 3 Nov
New place to stay
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Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Kissimmee
7 Bd/ 6 Ba/ Storey Lake (4585 Tb)
7 bedrooms, 10 beds, 6 bathrooms
1–6 Oct
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Superhost
Home in Clermont
2026 Themed 7BR house at Windsor Cay Resort
7 bedrooms, 10 beds, 6 bathrooms
17–22 Oct
New place to stay