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Search results; Over 1,000 homes in Winter Springs

Guest favourite
Guest suite in Winter Springs
Sierra Suite w/ Pool, Hot tub, and Sauna-Near UCF
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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4.89 out of 5 average rating, 147 reviews
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds
23–28 Aug
New place to stay
Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds
10–15 Aug
4.96 out of 5 average rating, 55 reviews
Top guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
9–16 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Longwood
The Tiki Palm | Screened Pool +Arcade + Mini Golf
4 bedrooms, 7 beds
8–13 Aug
5.0 out of 5 average rating, 19 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds
15–20 Aug
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed
18–23 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
14–19 Aug
5.0 out of 5 average rating, 104 reviews
Top guest favourite
Home in Osteen
Gorgeous St. Johns River home 3bdrm/2 bth
3 bedrooms, 3 beds
8–13 Aug
4.98 out of 5 average rating, 41 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds
9–14 Sept
New place to stay
Top guest favourite
Home in Sanford
Newly built, Calming Vibes. Close to downtown!
4 bedrooms, 6 beds
17–22 Aug
5.0 out of 5 average rating, 26 reviews
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds
21–26 Aug
New place to stay
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
14–19 Aug
New place to stay