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Search results; Over 1,000 homes in Maitland

Top guest favourite
Bungalow in Maitland
Maitland-Orlando Area, FL. Pool House Bungalow
1 bedroom, 2 beds, 1 private bathroom
29 Aug – 3 Sept
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4.88 out of 5 average rating, 622 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–29 Jul
Top guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
4.96 out of 5 average rating, 232 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
31 Jul – 5 Aug
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
5.0 out of 5 average rating, 63 reviews, 2 bedrooms, 2 beds, 2 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 Aug
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
New place to stay, 9 bedrooms, 12 beds, 6 bathrooms
28 Aug – 2 Sept
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 4 bathrooms
26–31 Jul
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
19–24 Dec
Superhost
Home in Kissimmee
7 BD/ 7.5 BA/ Sonoma Resort (3901 OA)
7 bedrooms, 7 beds, 7.5 bathrooms
2–7 Aug
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
5.0 out of 5 average rating, 133 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Top guest favourite
Home in Longwood
Central Florida Pool Home
4.96 out of 5 average rating, 53 reviews, 3 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
Superhost
Flat in Winter Park
The Grove
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Aug
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
5.0 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug