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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
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
17–22 Aug
New place to stay
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 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
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 21 reviews
Apartment in Casselberry
Cozy Private Apartment in Casselberry
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
Home in Orlando
Modern Cozy Home | BBQ | Free Parking | Near UCF
2 bedrooms, 2 queen beds, 1 bathroom
28 Aug – 2 Sept
New place to stay
Top guest favourite
Home in Longwood
The Tiki Palm | Screened Pool +Arcade + Mini Golf
4 bedrooms, 7 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
18–25 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Sanford
Sunny In Sanford w/Heated Pool
5 bedrooms, 9 beds, 2 bathrooms
17–22 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Osteen
Gorgeous St. Johns River home 3bdrm/2 bth
3 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
4.98 out of 5 average rating, 41 reviews
Superhost
Home in Kissimmee
9BR Pixar Theater Game Room | Pool Spa | Sleeps 27
9 bedrooms, 19 beds, 5 bathrooms
16–21 Aug
New place to stay
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
Superhost
Room in Sanford
Pondside Retreat Nana's Room Near SFB Airport
1 queen bed, 1 bathroom
1–6 Sept
New place to stay
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 4 reviews