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Search results; Over 1,000 homes in Winter Springs

Guest favorite
Guest suite in Winter Springs
Sierra Suite w/ Pool, Hot tub, and Sauna-Near UCF
1 bedroom, 1 bed, 1 private bath
Oct 1 – 6
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4.89 out of 5 average rating, 147 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 baths
Aug 17 – 22
New place to stay
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
New place to stay
Guest favorite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 baths
Sep 5 – 10
5.0 out of 5 average rating, 7 reviews
Top guest favorite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 21 reviews
Top guest favorite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 baths
Aug 14 – 21
5.0 out of 5 average rating, 24 reviews
Condo in Casselberry
Cozy Private Apartment in Casselberry
2 bedrooms, 2 queen beds, 1 bath
Aug 12 – 17
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 baths
Sep 2 – 7
5.0 out of 5 average rating, 29 reviews
Top guest favorite
Guest suite in Altamonte Springs
St.John suite
1 bedroom, 1 queen bed, 1 bath
Jan 31 – Feb 5
4.97 out of 5 average rating, 344 reviews
Top guest favorite
Home in Osteen
Gorgeous St. Johns River home 3bdrm/2 bth
3 bedrooms, 3 beds, 2 baths
Aug 20 – 25
4.98 out of 5 average rating, 41 reviews
Top guest favorite
Home in Longwood
The Tiki Palm | Screened Pool +Arcade + Mini Golf
4 bedrooms, 7 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 baths
Aug 12 – 17
5.0 out of 5 average rating, 5 reviews
Home in Deltona
Island Home — Pool, Kayak & Stunning Sunsets
4 bedrooms, 1 queen bed, 3 baths
Aug 17 – 22
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Sanford
Sunny In Sanford w/Heated Pool
5 bedrooms, 9 beds, 2 baths
Aug 17 – 22
4.92 out of 5 average rating, 13 reviews
Top guest favorite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
4.91 out of 5 average rating, 94 reviews
Top guest favorite
Home in Mount Dora
Langoon Lodge (4-BR 3-BA, 7 beds) Walk to DT&Lake
5 bedrooms, 8 beds, 3 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 21 reviews
Top guest favorite
Home in Tavares
Lake Dora Dream-Waterfront/Pool
4 bedrooms, 5 beds, 4 baths
Oct 11 – 16
4.97 out of 5 average rating, 157 reviews
Guest favorite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
5.0 out of 5 average rating, 104 reviews