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Search results; Over 1,000 homes in Winter Park

Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 beds, 2 private baths
Nov 7 – 13
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4.96 out of 5 average rating, 27 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
Top guest favorite
Apartment in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bath
Sep 18 – 23
5.0 out of 5 average rating, 11 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
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 baths
Aug 16 – 21
New place to stay
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 Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 baths
Aug 20 – 25
5.0 out of 5 average rating, 39 reviews
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
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 baths
Aug 20 – 25
5.0 out of 5 average rating, 63 reviews
Home in Orlando
Pool Home + BBQ Grill + Family Friendly
3 bedrooms, 4 beds, 2 baths
Aug 13 – 18
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 baths
Aug 22 – 27
5.0 out of 5 average rating, 12 reviews
Top guest favorite
Guesthouse in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bath
Nov 22 – 27
4.89 out of 5 average rating, 47 reviews
Guesthouse in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bath
Aug 13 – 18
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Treehouse in Orlando
Brand New Stylish & Unique Tree House!
1 bedroom, 2 beds, 1 bath
Aug 16 – 21
5.0 out of 5 average rating, 78 reviews
Top guest favorite
Guesthouse in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds, 1 bath
Aug 16 – 21
4.98 out of 5 average rating, 148 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 baths
Sep 14 – 19
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 baths
Aug 16 – 21
New place to stay