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Winter Park Vacation Rentals

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78 rentals in Winter Park.
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Ideal Location, Charming Home, Spacious w/ a Full Lap Pool!, vacation rental in Winter Park
Ideal Location, Charming Home, Spacious w/ a Full Lap Pool!, vacation rental in Winter Park
Ideal Location, Charming Home, Spacious w/ a Full Lap Pool!, vacation rental in Winter Park

Ideal Location, Charming Home, Spacious w/ a Full Lap Pool!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Casa Winter Park, vacation rental in Winter Park
Casa Winter Park, vacation rental in Winter Park
Casa Winter Park, vacation rental in Winter Park

Casa Winter Park

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Winter Park charm. Close to Park Ave, vacation rental in Winter Park
Winter Park charm. Close to Park Ave, vacation rental in Winter Park
Winter Park charm. Close to Park Ave, vacation rental in Winter Park

Winter Park charm. Close to Park Ave

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family home with flexible schedule, vacation rental in Winter Park
Family home with flexible schedule, vacation rental in Winter Park
Family home with flexible schedule, vacation rental in Winter Park

Family home with flexible schedule

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Amazing location- walk to everything, vacation rental in Winter Park
Amazing location- walk to everything, vacation rental in Winter Park
Amazing location- walk to everything, vacation rental in Winter Park

Amazing location- walk to everything

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Just Like Home... With A Pool!, vacation rental in Winter Park
Just Like Home... With A Pool!, vacation rental in Winter Park
Just Like Home... With A Pool!, vacation rental in Winter Park

Just Like Home... With A Pool!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock and More!, vacation rental in Winter Park
Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock and More!, vacation rental in Winter Park
Beautiful Retreat in the Heart of Winter Park - Office, Patio, Hammock and More!, vacation rental in Winter Park

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, vacation rental in Winter Park
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, vacation rental in Winter Park
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, vacation rental in Winter Park

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stroll to Park Avenue from Vintage Lake-View House, vacation rental in Winter Park
Stroll to Park Avenue from Vintage Lake-View House, vacation rental in Winter Park
Stroll to Park Avenue from Vintage Lake-View House, vacation rental in Winter Park

Stroll to Park Avenue from Vintage Lake-View House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful  Peaceful fenced yard home !, vacation rental in Winter Park
Beautiful  Peaceful fenced yard home !, vacation rental in Winter Park
Beautiful  Peaceful fenced yard home !, vacation rental in Winter Park

Beautiful Peaceful fenced yard home !

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Mid Century Modern Cottage in The Heart of Winter Park, vacation rental in Winter Park
Mid Century Modern Cottage in The Heart of Winter Park, vacation rental in Winter Park
Mid Century Modern Cottage in The Heart of Winter Park, vacation rental in Winter Park

Mid Century Modern Cottage in The Heart of Winter Park

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#3), vacation rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#3), vacation rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#3), vacation rental in Winter Park

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 Luxury, 1 block from Park Ave (#2), vacation rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#2), vacation rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#2), vacation rental in Winter Park

Mid Century Luxury, 1 block from Park Ave (#2)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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A curated stay in the Historic College Quarter  - 30 days minimum stay -, vacation rental in Winter Park
A curated stay in the Historic College Quarter  - 30 days minimum stay -, vacation rental in Winter Park
A curated stay in the Historic College Quarter  - 30 days minimum stay -, vacation rental in Winter Park

A curated stay in the Historic College Quarter - 30 days minimum stay -

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cute Guest House In Winter Park Minutes From Downtown in Car, vacation rental in Winter Park
Cute Guest House In Winter Park Minutes From Downtown in Car, vacation rental in Winter Park
Cute Guest House In Winter Park Minutes From Downtown in Car, vacation rental in Winter Park

Cute Guest House In Winter Park Minutes From Downtown in Car

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cute bungalow minutes walk from Park Avenue., vacation rental in Winter Park
Cute bungalow minutes walk from Park Avenue., vacation rental in Winter Park
Cute bungalow minutes walk from Park Avenue., vacation rental in Winter Park

Cute bungalow minutes walk from Park Avenue.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Breezy Pool Home!, vacation rental in Winter Park
Breezy Pool Home!, vacation rental in Winter Park
Breezy Pool Home!, vacation rental in Winter Park

Breezy Pool Home!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Winter Park Oasis, vacation rental in Winter Park
Winter Park Oasis, vacation rental in Winter Park
Winter Park Oasis, vacation rental in Winter Park

Winter Park Oasis

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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WeLive Winter Park / Spacious Enclave W/ Patio!, vacation rental in Winter Park
WeLive Winter Park / Spacious Enclave W/ Patio!, vacation rental in Winter Park
WeLive Winter Park / Spacious Enclave W/ Patio!, vacation rental in Winter Park

WeLive Winter Park / Spacious Enclave W/ Patio!

Rental Home
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Hidden Historic Jewel In Downtown Location!, vacation rental in Winter Park
Hidden Historic Jewel In Downtown Location!, vacation rental in Winter Park
Hidden Historic Jewel In Downtown Location!, vacation rental in Winter Park

Hidden Historic Jewel In Downtown Location!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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2br - 1000ft2 - Winter Park House, vacation rental in Winter Park
2br - 1000ft2 - Winter Park House, vacation rental in Winter Park
2br - 1000ft2 - Winter Park House, vacation rental in Winter Park

2br - 1000ft2 - Winter Park House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Beautiful Boho Brand New Winter Park Home!, vacation rental in Winter Park
Beautiful Boho Brand New Winter Park Home!, vacation rental in Winter Park
Beautiful Boho Brand New Winter Park Home!, vacation rental in Winter Park

Beautiful Boho Brand New Winter Park Home!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Best Home in Town !!, vacation rental in Winter Park
Best Home in Town !!, vacation rental in Winter Park
Best Home in Town !!, vacation rental in Winter Park

Best Home in Town !!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Chic Lakeside Midcentury Modern Retreat, vacation rental in Winter Park
Chic Lakeside Midcentury Modern Retreat, vacation rental in Winter Park
Chic Lakeside Midcentury Modern Retreat, vacation rental in Winter Park

Chic Lakeside Midcentury Modern Retreat

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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HOME AWAY FROM HOME in beautiful Winter Park, vacation rental in Winter Park
HOME AWAY FROM HOME in beautiful Winter Park, vacation rental in Winter Park
HOME AWAY FROM HOME in beautiful Winter Park, vacation rental in Winter Park

HOME AWAY FROM HOME in beautiful Winter Park

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Comfy Home in Winter Park, can accommodate up 6 guests!, vacation rental in Winter Park
Comfy Home in Winter Park, can accommodate up 6 guests!, vacation rental in Winter Park
Comfy Home in Winter Park, can accommodate up 6 guests!, vacation rental in Winter Park

Comfy Home in Winter Park, can accommodate up 6 guests!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Winter Park Bamboo Loft, vacation rental in Winter Park
Winter Park Bamboo Loft, vacation rental in Winter Park
Winter Park Bamboo Loft, vacation rental in Winter Park

Winter Park Bamboo Loft

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Three Blocks to Park Ave, 2 Blocks to WP Village!!!, vacation rental in Winter Park
Three Blocks to Park Ave, 2 Blocks to WP Village!!!, vacation rental in Winter Park
Three Blocks to Park Ave, 2 Blocks to WP Village!!!, vacation rental in Winter Park

Three Blocks to Park Ave, 2 Blocks to WP Village!!!

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

Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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The Mid-Century Modern Gem, vacation rental in Winter Park
The Mid-Century Modern Gem, vacation rental in Winter Park
The Mid-Century Modern Gem, vacation rental in Winter Park

The Mid-Century Modern Gem

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Relaxing, lake-view home near Park Avenue, vacation rental in Winter Park
Relaxing, lake-view home near Park Avenue, vacation rental in Winter Park
Relaxing, lake-view home near Park Avenue, vacation rental in Winter Park

Relaxing, lake-view home near Park Avenue

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stylish Boutique Guest House, vacation rental in Winter Park
Stylish Boutique Guest House, vacation rental in Winter Park
Stylish Boutique Guest House, vacation rental in Winter Park

Stylish Boutique Guest House

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stylish Boutique Guest house in Historic Winter Park., vacation rental in Winter Park
Stylish Boutique Guest house in Historic Winter Park., vacation rental in Winter Park
Stylish Boutique Guest house in Historic Winter Park., vacation rental in Winter Park

Stylish Boutique Guest house in Historic Winter Park.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Modern Mediterranean Oasis, vacation rental in Winter Park
Modern Mediterranean Oasis, vacation rental in Winter Park
Modern Mediterranean Oasis, vacation rental in Winter Park

Modern Mediterranean Oasis

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury King Condo min from everything!, vacation rental in Winter Park
Luxury King Condo min from everything!, vacation rental in Winter Park
Luxury King Condo min from everything!, vacation rental in Winter Park

Luxury King Condo min from everything!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Modern 2 Bedroom Apartment, vacation rental in Winter Park
Modern 2 Bedroom Apartment, vacation rental in Winter Park
Modern 2 Bedroom Apartment, vacation rental in Winter Park

Modern 2 Bedroom Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Luxury Living Just 3 Blocks From Park Ave!!!, vacation rental in Winter Park
Luxury Living Just 3 Blocks From Park Ave!!!, vacation rental in Winter Park
Luxury Living Just 3 Blocks From Park Ave!!!, vacation rental in Winter Park

Luxury Living Just 3 Blocks From Park Ave!!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, vacation rental in Winter Park
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, vacation rental in Winter Park
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, vacation rental in Winter Park

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, vacation rental in Winter Park
☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, vacation rental in Winter Park
☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, vacation rental in Winter Park

☀️ 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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Modern, luxurious 3 bedroom w/private pool in winter park close to everything, vacation rental in Winter Park
Modern, luxurious 3 bedroom w/private pool in winter park close to everything, vacation rental in Winter Park
Modern, luxurious 3 bedroom w/private pool in winter park close to everything, vacation rental in Winter Park

Modern, luxurious 3 bedroom w/private pool in winter park close to everything

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! Pet-Friendly Winter Park Home w/ Private Pool, vacation rental in Winter Park
NEW! Pet-Friendly Winter Park Home w/ Private Pool, vacation rental in Winter Park
NEW! Pet-Friendly Winter Park Home w/ Private Pool, vacation rental in Winter Park

NEW! Pet-Friendly Winter Park Home w/ Private Pool

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Light, Bright and Full of Delight! 2 Blocks to Park Ave, vacation rental in Winter Park
Light, Bright and Full of Delight! 2 Blocks to Park Ave, vacation rental in Winter Park
Light, Bright and Full of Delight! 2 Blocks to Park Ave, vacation rental in Winter Park

Light, Bright and Full of Delight! 2 Blocks to Park Ave

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Pondside Retreat with Koi in Charming Winter Park, FL, vacation rental in Winter Park
Pondside Retreat with Koi in Charming Winter Park, FL, vacation rental in Winter Park
Pondside Retreat with Koi in Charming Winter Park, FL, vacation rental in Winter Park

Pondside Retreat with Koi in Charming Winter Park, FL

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Winter Park Oasis, vacation rental in Winter Park
Winter Park Oasis, vacation rental in Winter Park
Winter Park Oasis, vacation rental in Winter Park

Winter Park Oasis

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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The Grand Palm Tropical Paradise � �Self check in⭐️, vacation rental in Winter Park
The Grand Palm Tropical Paradise � �Self check in⭐️, vacation rental in Winter Park
The Grand Palm Tropical Paradise � �Self check in⭐️, vacation rental in Winter Park

The Grand Palm Tropical Paradise � �Self check in⭐️

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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LUXURY FLAT IN WINTER PARK, vacation rental in Winter Park
LUXURY FLAT IN WINTER PARK, vacation rental in Winter Park
LUXURY FLAT IN WINTER PARK, vacation rental in Winter Park

LUXURY FLAT IN WINTER PARK

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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NEW *  Cozy Retreat Near Lake Killarney in Winter Park, vacation rental in Winter Park
NEW *  Cozy Retreat Near Lake Killarney in Winter Park, vacation rental in Winter Park
NEW *  Cozy Retreat Near Lake Killarney in Winter Park, vacation rental in Winter Park

NEW * Cozy Retreat Near Lake Killarney in Winter Park

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy Comfort In The Heart of Winter Park!, vacation rental in Winter Park
Cozy Comfort In The Heart of Winter Park!, vacation rental in Winter Park
Cozy Comfort In The Heart of Winter Park!, vacation rental in Winter Park

Cozy Comfort In The Heart of Winter Park!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lakefront Condo w/ Sunroom, Office, & Lakeside Pool, vacation rental in Winter Park
Lakefront Condo w/ Sunroom, Office, & Lakeside Pool, vacation rental in Winter Park
Lakefront Condo w/ Sunroom, Office, & Lakeside Pool, vacation rental in Winter Park

Lakefront Condo w/ Sunroom, Office, & Lakeside Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼, vacation rental in Winter Park
Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼, vacation rental in Winter Park
Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼, vacation rental in Winter Park

Cozy ★ 3 Bedroom Home in the ♥ of Winter Park! ☼

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Frequently Asked Questions about Winter Park