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Maitland House Rentals

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50 rentals in Maitland.
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Temporary living that feels like home where you can relax and be yourself., vacation rental in Maitland

Temporary living that feels like home where you can relax and be yourself.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog, vacation rental in Maitland

Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Bella, vacation rental in Maitland

Casa Bella

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Fresh & Modern Home, Sweet Home  DISCOUNTS AVAILABLE, vacation rental in Maitland

Fresh & Modern Home, Sweet Home DISCOUNTS AVAILABLE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Large living area, tropical backyard with swimming pool & covered  back porch, vacation rental in Maitland

Large living area, tropical backyard with swimming pool & covered back porch

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxury MidCentury Winter Park/Maitland/Orlando, vacation rental in Maitland

Luxury MidCentury Winter Park/Maitland/Orlando

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Orlando area pool hame in Maitland, vacation rental in Maitland

Orlando area pool hame in Maitland

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Warm and Inviting. Ideally located, 3BR/2BA Home, vacation rental in Maitland

Warm and Inviting. Ideally located, 3BR/2BA Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Orlando Group Cottage Sleep 14 Guests, vacation rental in Maitland

Orlando Group Cottage Sleep 14 Guests

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Affordable, convenient and private family space, vacation rental in Maitland

Affordable, convenient and private family space

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Private Room Master Suite, vacation rental in Maitland

Amazing Private Room Master Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Home Located Between Theme Parks and Beaches., vacation rental in Maitland

Charming Home Located Between Theme Parks and Beaches.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family home with flexible schedule, vacation rental in Maitland

Family home with flexible schedule

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!, vacation rental in Maitland

Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stroll to Park Avenue from Vintage Lake-View House, vacation rental in Maitland

Stroll to Park Avenue from Vintage Lake-View House

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely, Spacious, Comfortable house in Altamonte Springs. Very clean ., vacation rental in Maitland

Lovely, Spacious, Comfortable house in Altamonte Springs. Very clean .

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Winter Park charm. Close to Park Ave, vacation rental in Maitland

Winter Park charm. Close to Park Ave

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Winter Park, vacation rental in Maitland

Casa Winter Park

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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PRIVATE Luxury Pool / Smart-home, vacation rental in Maitland

PRIVATE Luxury Pool / Smart-home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Botanical Gardens - Orlando / Winter Park, vacation rental in Maitland

Botanical Gardens - Orlando / Winter Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park-College Park-Orlando-1, vacation rental in Maitland

Winter Park-College Park-Orlando-1

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2br - 1000ft2 - Winter Park House, vacation rental in Maitland

2br - 1000ft2 - Winter Park House

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Chic Lakeside Midcentury Modern Retreat, vacation rental in Maitland

Chic Lakeside Midcentury Modern Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Home, Sweet Home Orlando, vacation rental in Maitland

Home, Sweet Home Orlando

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Shed in Downtown Orlando, vacation rental in Maitland

The Shed in Downtown Orlando

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ivanhoe Village Quiet Home, Walk to Restaurants, Shops, Hospital, Everything!, vacation rental in Maitland

Ivanhoe Village Quiet Home, Walk to Restaurants, Shops, Hospital, Everything!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A great little apartment in College Park, Orlando., vacation rental in Maitland

A great little apartment in College Park, Orlando.

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Walk to Disney world! Full kitchen sleeps 6!, vacation rental in Maitland

Walk to Disney world! Full kitchen sleeps 6!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A great loft apartment in College Park, Orlando., vacation rental in Maitland

A great loft apartment in College Park, Orlando.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Cottage on Lake Fairview, Orlando., vacation rental in Maitland

The Cottage on Lake Fairview, Orlando.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fern Park House w/Pool - New Patio & Fire Pit!, vacation rental in Maitland

Fern Park House w/Pool - New Patio & Fire Pit!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Winter Park Home With Hints Of Florida Keys, vacation rental in Maitland

Winter Park Home With Hints Of Florida Keys

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Winter Park-College Park-Orlando -2, vacation rental in Maitland

Winter Park-College Park-Orlando -2

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Garage Apartment Just North Of Downtown, vacation rental in Maitland

Beautiful Garage Apartment Just North Of Downtown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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'Lakeside' in old Winter Park (exclusive 32789zip), vacation rental in Maitland

'Lakeside' in old Winter Park (exclusive 32789zip)

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Travel Themed Getaway Orlando / Winter Park, vacation rental in Maitland

Travel Themed Getaway Orlando / Winter Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Surfs Up Theme - Winter Park/Orlando, vacation rental in Maitland

Surfs Up Theme - Winter Park/Orlando

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lakefront Luxury Furnished  Split Floor Plan First Floor Condo, vacation rental in Maitland

Lakefront Luxury Furnished Split Floor Plan First Floor Condo

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Casa Vista Verde I Dream House & Vacation Paradise Orlando Area 5/2 Pool Disney, vacation rental in Maitland

Casa Vista Verde I Dream House & Vacation Paradise Orlando Area 5/2 Pool Disney

5 bedrooms
2 bathrooms
Sleeps 20
Match: Sleeps
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Storey Lake Resort 21 - townhouse with private pool near Disney, vacation rental in Maitland

Storey Lake Resort 21 - townhouse with private pool near Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Elegant College Park Cottage w/ Patio & Gas Grill!, vacation rental in Maitland

Elegant College Park Cottage w/ Patio & Gas Grill!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Orlando Area 4BR/2BA Home w/Jacuzzi & communal pool Disney Unioversal Daytona, vacation rental in Maitland

Orlando Area 4BR/2BA Home w/Jacuzzi & communal pool Disney Unioversal Daytona

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Altamonte Springs Home w/Canoe on Lake Marion, vacation rental in Maitland

Altamonte Springs Home w/Canoe on Lake Marion

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Orlando Area 3BR/2BA/2Ki nearby New City pool, Jacuzzi Disney Universal Daytona, vacation rental in Maitland

Orlando Area 3BR/2BA/2Ki nearby New City pool, Jacuzzi Disney Universal Daytona

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Pet Friendly Business Travelers 2/1 House, Close to Everything Orlando, vacation rental in Maitland

Pet Friendly Business Travelers 2/1 House, Close to Everything Orlando

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Old World Charm of College Park/Winter Park Preview listing, vacation rental in Maitland

Old World Charm of College Park/Winter Park Preview listing

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, vacation rental in Maitland

☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lounge on Blue Velvet Couches at a Charming Hideaway, vacation rental in Maitland

Lounge on Blue Velvet Couches at a Charming Hideaway

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing location- walk to everything, vacation rental in Maitland

Amazing location- walk to everything

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Winter Park, Florida Luxury Vacation Rental, vacation rental in Maitland

Winter Park, Florida Luxury Vacation Rental

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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