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Maitland Holiday 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., holiday 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, holiday 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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Large living area, tropical backyard with swimming pool & covered  back porch, holiday rental in Maitland

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

2 bedrooms
2 bathrooms
Sleeps 5
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Warm and Inviting. Ideally located, 3BR/2BA Home, holiday rental in Maitland

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Affordable, convenient and private family space, holiday rental in Maitland

Affordable, convenient and private family space

1 bedroom
1 bathroom
Sleeps 4
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Amazing Private Room Master Suite, holiday rental in Maitland

Amazing Private Room Master Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!, holiday rental in Maitland

Casa Aloma - Elegant Winter Park House with Great Pool and Huge Backyard!!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming Home Located Between Theme Parks and Beaches., holiday rental in Maitland

Charming Home Located Between Theme Parks and Beaches.

3 bedrooms
2 bathrooms
Sleeps 8
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Family home with flexible schedule, holiday rental in Maitland

Family home with flexible schedule

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Just Like Home... With A Pool!, holiday rental in Maitland

Just Like Home... With A Pool!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Winter Park charm. Close to Park Ave, holiday rental in Maitland

Winter Park charm. Close to Park Ave

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock & More!, holiday rental in Maitland

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

2 bedrooms
2 bathrooms
Sleeps 4
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Casa Winter Park, holiday rental in Maitland

Casa Winter Park

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stroll to Park Avenue from Vintage Lake-View House, holiday rental in Maitland

Stroll to Park Avenue from Vintage Lake-View House

2 bedrooms
2 bathrooms
Sleeps 6
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PRIVATE Luxury Pool / Smart-home, holiday rental in Maitland

PRIVATE Luxury Pool / Smart-home

3 bedrooms
2 bathrooms
Sleeps 10
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Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park, holiday rental in Maitland

Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park

2 bedrooms
1 bathroom
Sleeps 6
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Lovely, Spacious, Comfortable house in Altamonte Springs. Very clean ., holiday rental in Maitland

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

4 bedrooms
2 bathrooms
Sleeps 9
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Modern Garden Suite!, holiday rental in Maitland

Modern Garden Suite!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Ivanhoe Village Quiet Home, Walk to Restaurants, Shops, Hospital, Everything!, holiday rental in Maitland

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

1 bedroom
1 bathroom
Sleeps 2
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Amazing location- walk to everything, holiday rental in Maitland

Amazing location- walk to everything

2 bedrooms
2 bathrooms
Sleeps 5
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Lakeview 3 BR Villa with large private pool nestled into Florida's nature, holiday rental in Maitland

Lakeview 3 BR Villa with large private pool nestled into Florida's nature

3 bedrooms
2 bathrooms
Sleeps 6
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Old World Charm of College Park/Winter Park Preview listing, holiday rental in Maitland

Old World Charm of College Park/Winter Park Preview listing

3 bedrooms
2 bathrooms
Sleeps 6
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Florida Bliss,the  whole Duplex a 1/4 of an acre of tropical Bliss to enjoy!!!, holiday rental in Maitland

Florida Bliss,the whole Duplex a 1/4 of an acre of tropical Bliss to enjoy!!!

4 bedrooms
2 bathrooms
Sleeps 8
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Winter Park-College Park-Orlando-1, holiday rental in Maitland

Winter Park-College Park-Orlando-1

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

2br - 1000ft2 - Winter Park House

2 bedrooms
2 bathrooms
Sleeps 5
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Chic Lakeside Midcentury Modern Retreat, holiday rental in Maitland

Chic Lakeside Midcentury Modern Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New on the Market!  Spotless Lakeside Home, holiday rental in Maitland

New on the Market! Spotless Lakeside Home

3 bedrooms
2 bathrooms
Sleeps 6
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Home, Sweet Home Orlando, holiday rental in Maitland

Home, Sweet Home Orlando

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

The Shed in Downtown Orlando

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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HOME AWAY FROM HOME in beautiful Winter Park, holiday rental in Maitland

HOME AWAY FROM HOME in beautiful Winter Park

2 bedrooms
2 bathrooms
Sleeps 7
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Rest, Swim, and Relax at our Cozy Lakefront Tiki Bungalow, holiday rental in Maitland

Rest, Swim, and Relax at our Cozy Lakefront Tiki Bungalow

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walk to Disney world! Full kitchen sleeps 6!, holiday rental in Maitland

Walk to Disney world! Full kitchen sleeps 6!

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

Winter Park-College Park-Orlando -2

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

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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2br - 2200ft2 - Beautiful one story 2 bed/3bath, holiday rental in Maitland

2br - 2200ft2 - Beautiful one story 2 bed/3bath

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Lakefront Luxury Furnished  Split Floor Plan First Floor Condo, holiday rental in Maitland

Lakefront Luxury Furnished Split Floor Plan First Floor Condo

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quiet Home Near Shopping & 15 Miles From Orlando!, holiday rental in Maitland

Quiet Home Near Shopping & 15 Miles From Orlando!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Vista Verde I Dream House & Vacation Paradise Orlando Area 5/2 Pool Disney, holiday 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, holiday 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!, holiday 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 5BR/2BA Home w/ Jacuzzi!, holiday rental in Maitland

Orlando Area 5BR/2BA Home w/ Jacuzzi!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Orlando Area 4BR/2BA Home w/Jacuzzi & communal pool Disney Unioversal Daytona, holiday 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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Lakeview Orlando Oasis, holiday rental in Maitland

Lakeview Orlando Oasis

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Altamonte Springs Home w/Canoe on Lake Marion, holiday rental in Maitland

Altamonte Springs Home w/Canoe on Lake Marion

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bijzonder overnachten in de natuur van Orlando, holiday rental in Maitland

Bijzonder overnachten in de natuur van Orlando

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Orlando Area 3BR/2BA/2Ki nearby New City pool, Jacuzzi Disney Universal Daytona, holiday 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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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Maitland

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Orlando Area 4/2 Pool Disney Universal Daytona, holiday rental in Maitland

Orlando Area 4/2 Pool Disney Universal Daytona

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Winter Park, Florida Luxury Vacation Rental, holiday rental in Maitland

Winter Park, Florida Luxury Vacation Rental

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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