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Search results; Over 1,000 places in Winter Park

Villa in Winter Park
Balfour Villa
22 – 27 Apr
4.75 out of 5 average rating, 75 reviews
Superhost
Villa in Winter Park
As close as you can stay to Rollins College!
2 beds
19 – 24 Apr
4.91 out of 5 average rating, 34 reviews
Villa in Winter Park
Charming Winter Park 3 Bedroom Villa with Pool
4 beds
21 – 26 Apr
4.71 out of 5 average rating, 21 reviews
Guest favourite
Villa in Casselberry
Entire house 4 bedrooms 2 bathrooms, Pool & Patio.
4 queen beds
27 May – 1 June
4.93 out of 5 average rating, 58 reviews
Guest favourite
Villa in Orlando
At Lakes Upscale Villa/Near to Downtown Orlando
6 beds
27 Apr – 2 May
4.94 out of 5 average rating, 63 reviews
Superhost
Villa in Altamonte Springs
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
1 queen bed
29 Apr – 4 May
4.77 out of 5 average rating, 70 reviews
Superhost
Villa in Orlando
4800 sf 7 Room Lakefront Estate
12 beds
22 – 27 Apr
4.94 out of 5 average rating, 48 reviews
Guest favourite
Villa in Orlando
Entire Historic Retreat @onceuponasuite Downtown
4 beds
17 – 22 May
4.91 out of 5 average rating, 46 reviews
Guest favourite
Villa in Altamonte Springs
Sweet & cozy vacation home!
4 – 9 May
4.98 out of 5 average rating, 84 reviews
Superhost
Villa in Orlando
Private Oasis 5 mi to Universal - Heated Pool
9 beds
21 – 26 Apr
4.78 out of 5 average rating, 130 reviews
Villa in Windermere
Rustic Hideaway - Great Location + Pet Friendly!
6 beds
11 – 16 May
4.5 out of 5 average rating, 8 reviews
Villa in Oviedo
Luxurious 6 bedroom inc Master Suite w/ Wet Room
6 beds
22 – 27 Apr
4.8 out of 5 average rating, 10 reviews
Guest favourite
Villa in St. Cloud
With tree house, Surprising Tropical-style resort
7 beds
28 Apr – 3 May
4.9 out of 5 average rating, 39 reviews
Guest favourite
Villa in Kissimmee
Disney-Themed Home w/ Game Room & Private Hot Tub!
8 beds
23 – 28 Apr
4.99 out of 5 average rating, 153 reviews
Guest favourite
Villa in Kissimmee
Lakeview Luxury Villa with Everything!
13 beds
19 – 24 Apr
4.95 out of 5 average rating, 38 reviews
Superhost
Villa in Orlando
Luxury: PVT Pool, Game room, PS5 & Summer Kitchen
13 beds
10 – 15 May
5.0 out of 5 average rating, 5 reviews
Superhost
Villa in Orlando
Luxury: Jacuzzi, Themed Venues, Game room & more
18 beds
21 – 26 Apr
New place to stay
Guest favourite
Villa in Davenport
Blue Paradise-Sleeps 32- FREE EV Charger-Theater
22 beds
13 – 18 May
4.95 out of 5 average rating, 59 reviews
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