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Search results; Over 1,000 homes in Longwood

Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 private bathrooms
15–20 Sept
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4.95 out of 5 average rating, 56 reviews
Top guest favourite
Home in Longwood
The Tiki Palm | Private Resort + Arcade + Pool
4 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
16–23 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 97 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Longwood
The Laurel - Beautiful cottage on private acreage
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 55 reviews
Home in Sanford
Walk Everywhere! Historic Sanford Home w/ Patio
2 bedrooms, 2 beds, 1.5 bathrooms
11–16 Oct
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 42 reviews
Guest favourite
Guest house in Sanford
The Nook
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
14–19 Jan
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed, 1 bathroom
18–23 Nov
4.98 out of 5 average rating, 482 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 184 reviews
Home in Sanford
Parks2Coast Trail Hideaway
3 bedrooms, 4 beds, 2 bathrooms
6–11 Dec
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 7 reviews
Hotel in Lake Mary
*30 miles From Orlando + Free Breakfast & Pool
3 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 215 reviews
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Sanford
Bright & Cozy 3BR Retreat with Timeless Charm
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Guest house in Orlando
Amazing New Pool House!
1 bedroom, 2 beds, 1 bathroom
23–28 Nov
4.98 out of 5 average rating, 112 reviews