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Maitland Holiday Apartments

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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 House
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 House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Bella

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Large living area, tropical backyard with swimming pool & covered back porch

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Comfy 3 Bedroom Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Affordable, convenient and private family space

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Affordable, convenient and private family space

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Private Room Master Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Warm and Inviting. Ideally located, 3BR/2BA Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hotel in Orlando Maitland

Holiday Rental House
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 House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Family home with flexible schedule

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Casa Winter Park

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Winter Park charm. Close to Park Ave

Holiday Rental House
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 House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Altamonte Springs Home w/Canoe on Lake Marion

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing location- walk to everything

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stroll to Park Avenue from Vintage Lake-View House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ELEGANT ESTATE VACATION RESORT HOME 'THE CHLOE'

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#3)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Mid Century Modern Cottage in The Heart of Winter Park

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lovely, Spacious, Comfortable house in Altamonte Springs. Very clean .

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cute Guest House In Our Backyard Winter Park Mins

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#2)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Amazing Altamonte Springs

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage Retreat in the City

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cute bungalow minutes walk from Park Avenue.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Orlando Area 2BR/1BA Duplex near New City pool, Jacuzzi Disney Universal Daytona

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Old World Charm of College Park/Winter Park Preview listing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Orlando Area 4BR/2BA Home w/Jacuzzi & New Communal pool Disney Universal Daytona

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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8th Green Cottage 'A relaxing Oasis in the city'

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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WeLive Winter Park / Spacious Enclave W/ Patio!

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Hidden Historic Jewel In Downtown Location!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Comfy Home in Winter Park, can accommodate up 6 guests!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ELEGANT ESTATE VACATION RESORT HOME 'THE OLIVIA'

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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2br - 1000ft2 - Winter Park House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Chic Lakeside Midcentury Modern Retreat

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Rustic 1950s Home on Small Lake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Luxury Furnished Split Floor Plan First Floor Condo

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Orlando Area 4BR/2BA Home w/Jacuzzi & communal pool Disney Unioversal Daytona

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Orlando Area 3BR/2BA/2Ki nearby New City pool, Jacuzzi Disney Universal Daytona

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Altamonte Springs Orlando hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy Comfort In The Heart of Winter Park!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Quite/Cozy 2+2 Apartment in Maitland // 120

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Lakefront Community Condo w/ Sunroom, Lakeside Pool and Waterfront Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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♛~Lovely Lakeside 3BR Home w/ Private Pool+Dock~♛

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Relaxing, lake-view home near Park Avenue

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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