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Search results; Over 1,000 homes in Longwood

Guest favourite
Room in Longwood
More For Your Money
1 bedroom, 1 bed, 1 private bathroom
19–24 Aug
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4.93 out of 5 average rating, 264 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
20–27 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
20–25 Aug
New place to stay
Home in Lake Mary
Southern Homestead
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 21 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Longwood
The Laurel - Beautiful cottage on private acreage
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 55 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
Guest favourite
Home in Sanford
Sunny In Sanford w/Heated Pool
5 bedrooms, 9 beds, 2 bathrooms
21–26 Aug
4.93 out of 5 average rating, 14 reviews
Townhouse in Kissimmee
Disney Retreat w/ Private Pool & Resort Access
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Aug
New place to stay
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Sanford
The Getaway - 1 BR/1 BA on 5 acres
1 queen bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 5 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
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Altamonte Springs
St.John suite
1 bedroom, 1 queen bed, 1 bathroom
31 Jan – 5 Feb
4.97 out of 5 average rating, 344 reviews
Guest favourite
Guest house in Sanford
The Nook
1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 10 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, 5 reviews