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Search results; Over 1,000 homes in Longwood

Top guest favourite
Home in Longwood
The Laurel - Beautiful cottage on private acreage
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
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5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Longwood
The Tiki Palm | Screened Pool +Arcade + Mini Golf
4 bedrooms, 7 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
23–30 Aug
5.0 out of 5 average rating, 24 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Mount Dora
Langoon Lodge (4-BR 3-BA, 7 beds) Walk to DT&Lake
5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 180 reviews
Superhost
Home in Kissimmee
7 Bd/ 6 Ba/ Storey Lake (4585 Tb)
7 bedrooms, 10 beds, 6 bathrooms
26 Sept – 1 Oct
New place to stay
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Home in Tavares
Lake Dora Dream-Waterfront/Pool
4 bedrooms, 5 beds, 4 bathrooms
25–30 Oct
4.97 out of 5 average rating, 159 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 reviews